Sulfamoyl compounds and agricultural and horticultural fungicides

ABSTRACT

A sulfamoyl compound of the general formulae (1): 
                         
wherein
         R 1  and R 2  are each independently C 1-4  alkyl, or R 1  and R 2  together are C 4-6  alkylene or C 4-6  alkyleneoxy,   Y is H, halogen, C 1-8  alkyl, C 1-8  alkoxy, C 1-8  alkylthio, C 1-8  haloalkyl, C 1-8  haloalkoxy or C 1-8  haloalkylthio,   A is a predetermined heterocyclic group,   B is a predetermined heterocyclic group which is identical with or different from A,   W is a chemical bond or O,   V is O or S,   D, E, F and G are each independently N, CR 7 , CR 8 , CR 9  or CR 10 , and   R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10  and R 11  are each independently predetermined group such as H, or an unsubstituted or substituted aliphatic, aromatic or heterocyclic group.       
     The sulfamoyl compound is useful as an agricultural and horticultural fungicide.

This is a Division of Application Ser. No. 09/964,357 filed Sep. 28, 2001, now U.S. Pat No. 6,620,812 which in turn is a Division of Ser. No. 09/529,817, filed Jun. 2, 2000 now U.S. Pat. No. 6,350,748, which is the U.S. National Stage of International Application No. PCT/JP98/048085 filed Oct. 23, 1998. The entire disclosure of the prior applications are hereby incorporated by reference herein in their entirety.

TECHNICAL FIELD

The present invention relates to novel sulfamoyl compounds, and agricultural chemicals (insecticides, fungicides, herbicides, plant growth controlling agents and the like.), particularly agricultural and horticultural fungicides.

BACKGROUND ART

JP-A-3-170464, JP-A-6-32785, JP-A-7-2803 and JP-A-7-215971 describe that certain sulfamoyl compounds have bactericidal activities.

Even the compounds described in the above-described early publications are unsatisfactory in potency and residual effectiveness, thus developments of more useful agricultural and horticultural fungicide have been desired.

DISCLOSURE OF THE INVENTION

Under the circumstances, the present inventors have made extensive research with a view to developing excellent fungicide and, as a result, have found that novel sulfamoyl compounds have remarkable controlling activity as agricultural and horticultural fungicide, thus accomplishing the present invention.

That is, the present invention relates to [1] to [38].

-   [1] A sulfamoyl compound of the general formulae (1):

 wherein

R¹ and R² are each independently C₁₋₄ alkyl, or R¹ and R² together are C₄₋₆ alkylene or C₄₋₆ alkyleneoxy,

Y is H, halogen, C₁₋₈ alkyl, C₁₋₈ alkoxy, C₁₋₈ alkylthio, C₁₋₈ haloalkyl, C₁₋₈ haloalkoxy or C₁₋₈ haloalkylthio,

A is

B is A-1 to A-10, or

W is a chemical bond or O,

V is O or S.

D, E, F and G are each independently N. CR⁷, CR⁸, CR⁹ or CR¹⁰, and

R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰ and R¹¹ are each independently H, C₁₋₈ alkyl, C₃₋₈ cycloalkyl, C₂₋₈ alkenyl, C₅₋₈ cycloalkenyl, C₂₋₈ alkynyl, C₁₋₈ alkoxy, C₃₋₈ cycloalkyloxy, C₅₋₈ cycloalkenyloxy, C₂₋₈ alkenyloxy, C₂₋₈ alkynyloxy, C₁₋₈ alkylthio, C₃₋₈ cycloalkylthio, C₅₋₈ cycloalkenylthio, C₂₋₈ alkenylthio, C₂₋₈ alkynylthio, C₁₋₈ haloalkyl, C₁₋₈ haloalkoxy, C₁₋₈ haloalkylthio, C₂₋₈ haloalkenyl, C₂₋₈ haloalkenyloxy, C₂₋₈a haloalkenylthio, C₂₋₈ haloalkynyl, C₂₋₈ haloalkynyloxy, C₂₋₈ haloalkynylthio, phenyl which may be substituted (the kinds of substituent include halogen, C₁₋₈ alkyl, C₁₋₈ haloalkyl, C₁₋₈ alkoxy, C₁₋₈ haloalkoxy, C₁₋₈ alkylthio, C₁₋₈ haloalkylthio, C₁₋₆ alkylsulfoxy, C₁₋₆ alkylsulfonyl, CN, NO₂ and C₁₋₆ alkoxycarbonyl, the number of the substituents is 1 to 5, and the substituents may be identical or different.), phenyl C₁₋₄ alkyl which may be substituted, benzylthio which may be substituted, benzyloxy which may be substituted, phenoxy C₁₋₄ alkyl which may be substituted, phenoxy which may be substituted, phenylthio C₁₋₄ alkyl which may be substituted, phenylthio which may be substituted, benzoyl which may be substituted, benzoyl C₁₋₄ alkyl which may be substituted, benzoyloxy which may be substituted, benzoyloxy C₁₋₄ alkyl which may be substituted, naphthyl which may be substituted, 5- or 6-membered heterocyclic ring which may b substituted, C₁₋₈ hydroxyalkyl, C₁₋₈ hydroxyhaloalkyl, C₁₋₆ alkoxy C₁₋₄ alkyl, C₁₋₆ haloalkoxy C₁₋₄ alkyl, C₁₋₆ haloalkylthio C₁₋₄ alkyl, C₁₋₁₀ dialkoxy C₁₋₄ alkyl, C₁₋₃ alkylenedioxy C₁₋₄ alkyl, C₁₋₆ alkylthio C₁₋₄ alkyl, C₁₋₁₀ dialkylthio C₁₋₄ alkyl, C₁₋₃ alkylenedithio C₁₋₄ alkyl, C₁₋₆ alkoxycarbonyl, C₁₋₆ haloalkoxycarbonyl, C₁₋₆ alkoxyoxalyl, CHO, CO₂H, C₁₋₆ alkoxycarbonyl C₁₋₄ alkyl, C₁₋₆ haloalkoxycarbonyl C₁₋₄ alkyl, NH₂, C₁₋₆ alkylamino, C₁₋₆ alkylcarbonylamino, C₁₋₆ alkylcarbonylamino C₁₋₄ alkyl, C₁₋₆ haloalkylcarbonylamino, C₁₋₆ haloalkylcarbonylamino C₁₋₄ alkyl, C₁₋₆ alkoxycarbonylamino, C₁₋₆ alkoxycarbonylamino C₁₋₄ alkyl, C₁₋₆ alkylsulfonylamino, C₁₋₆ alkylsulfonylamino C₁₋₄ alkyl, C₁₋₆ haloalkylsulfonylamino, C₁₋₆ haloalkylsulfonylamino C₁₋₄ alkyl, C₁₋₆ dialkylamino, C₁₋₆ dialkylamino C₁₋₄ alkyl, C₁₋₆ dialkylaminocarbonyl, C₁₋₆ dialkylaminocarbonyl C₁₋₄ alkyl, C₂₋₆ alkyleneimino, C₂₋₆ alkyleneimino C₁₋₄ alkyl, C₂₋₆ alkyleneiminocarbonyl, C₂₋₆ alkyleneiminocarbonyl C₁₋₄ alkyl, C₁₋₆ alkylcarbonyl, C₁₋₆ alkylcarbonyloxy, C₁₋₆ haloalkylcarbonyl, C₁₋₆ haloalkylcarbonyloxy, C₁₋₆ alkylcarbonyl C₁₋₄ alkyl, C₁₋₆ alkylcarbonyloxy C₁₋₄ alkyl, C₁₋₆ haloalkylcarbonyl C₁₋₄ alkyl, C₁₋₆ haloalkylcarbonyloxy C₁₋₄ alkyl, hydroxyimino C₁₋₄ alkyl, C₁₋₆ alkoxyimino C₁₋₄ alkyl, C₁₋₆ alkylcarbonyloxyimino C₁₋₄ alkyl, C₁₋₆ alkylsulfonyloxyimino C₁₋₄ alkyl, C₁₋₆ alkylsulfoxy, C₁₋₆ haloalkylsulfoxy, C₁₋₆ alkylsulfoxy C₁₋₄ alkyl, C₁₋₆ haloalkylsulfoxy C₁₋₄ alkyl, C₁₋₆ alkylsulfonyl, C₁₋₆ haloalkylsulfonyl, C₁₋₆ alkylsulfonyl C₁₋₄ alkyl, C₁₋₆ haloalkylsulfonyl C₁₋₄ alkyl, C₁₋₆ alkylsulfonyloxy, C₁₋₆ haloalkylsulfonyloxy, C₁₋₆ alkylsulfonyloxy C₁₋₄ alkyl, C₁₋₆ haloalkylsulfonyloxy C₁₋₄ alkyl, C₁₋₆ haloalkoxysulfonyl, C₁₋₆ haloalkoxysulfonyl C₁₋₄ alkyl, C₁₋₆ dialkylsulfamoyl, C₁₋₆ dialkylsulfamoyl C₁₋₄ alkyl, C₁₋₆ alkoxysulfonyl, C₁₋₆ alkoxysulfonyl C₁₋₄ alkyl, C₂₋₆ cyanoalkyl, CN, C₁₋₆ thiocarbamoyl, C₁₋₆ nitroalkyl, NO₂ or halogen, or two of R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰ and R¹¹ together are C₁₋₃ alkylenedioxy which may be substituted, or C₃₋₆ alkylene.

-   [2] A sulfamoyl compound described in [1] above, in which A is A-1. -   [3] A sulfamoyl compound described in [1] above, in which A is A-2. -   [4] A sulfamoyl compound described in [1] above, in which A is A-3. -   [5] A sulfamoyl compound described in [1] above, in which A is A-4. -   [6] A sulfamoyl compound described in [1] above, in which A is A-5     or A-6. -   [7] A sulfamoyl compound described in [1] above, in which A is A-7     or A-8. -   [8] A sulfamoyl compound described in [1] above, in which A is A-9     or A-10. -   [9] A sulfamoyl compound described in [1] above, in which B is B-1. -   [10] A sulfamoyl compound described in [1] above, in which B is B-2. -   [11] A sulfamoyl compound described in [1] above, in which B is B-3     or B-4. -   [12] A sulfamoyl compound described in [1] above, in which B is B-5. -   [13] A sulfamoyl compound described in [1] above, in which B is B-6     or B-7. -   [14] A sulfamoyl compound described in [1] above, in which B is B-8     or B-9. -   [15] A sulfamoyl compound described in [1] above, in which B is     B-10. -   [16] A sulfamoyl compound described in [1] above, in which R¹ and R²     are Me, Y is H, W is a chemical bond, A is A-1, D, E, F and G are     CR⁷, CR⁸, CR⁹ or CR¹⁰, and R³ is C₁₋₈ alkylthio. -   [17] A sulfamoyl compound described in [1] above, in which R¹ and R²     are Me, Y is H, W is a chemical bond, A is A-1, D, E, F and G are     CR⁷, CR₈, CR⁹ or CR¹⁰, and R³ is C₁₋₈ alkyl. -   [18] A sulfamoyl compound described in [1] above, in which R¹ and R²     are Me, Y is H, W is a chemical bond, A is A-1, D, E, F and G are     CR⁷, CR⁸, CR⁹ or CR¹⁰, and R³ is C₁₋₈ haloalkyl. -   [19] A sulfamoyl compound described in [1] above, in which R¹ and R²     are Me, Y is H, W is a chemical bond, A is A-1, D, E, F and G are     CR⁷, CR⁸, CR⁹ or CR¹⁰, and R³ is halogen. -   [20] A sulfamoyl compound described in [1] above, in which R¹ and R²     are Me, Y is H, W is a chemical bond, A is A-1, D, E, F and G are     CR⁷, CR⁸, CR⁹ or CR¹⁰, and R³ is H. -   [21] A sulfamoyl compound described in [1] above, in which R¹ and R²     are Me, Y is H, W is a chemical bond, A is A-1, D, E, F and G are     CR⁷, CR⁸, CR⁹ or CR¹⁰, and R³ is CN. -   [22] A sulfamoyl compound described in [1] above, in which R¹ and R²     are Me, Y is H, W is a chemical bond, A is A-2, D, E, F and G are     CR⁷, CR⁸, CR⁹ or CR¹⁰, and any of R³, R⁴, R⁵ and R⁶ is H. -   [23] A sulfamoyl compound described in [1] above, in which R¹ and R²     are Me, Y is H, W is a chemical bond, A is A-4, and at least one of     R³, R⁴, R⁵ and R⁶ is phenyl which may be substituted. -   [24] A sulfamoyl compound described in [1] above, in which R¹ and R²     are Me, Y is H, W is a chemical bond, and B is B-1. -   [25] A sulfamoyl compound described in [1] above, in which R¹ and R²     are Me, Y is H, W is a chemical bond, A is A-1, D, E, F and G ar     CR⁷, CR⁸, CR⁹ or CR¹⁰, R³ is C₁₋₈, alkyl, and R⁴ is halogen. -   [26] A sulfamoyl compound described in [1] above, in which R¹ and R²     are Me, Y is H, W is a chemical bond, A is A-1, D, E, F and G are     CR⁷, CR⁸, CR⁹ or CR¹⁰, and any of R³ and R⁴ is halogen. -   [27] A sulfamoyl compound described in [1] above, in which R¹ and R²     are Me, Y is H, W is a chemical bond, A is A-1, D, E, F and G are     CR⁷, CR⁸, CR⁹ or CR¹⁰, R³ is C₁₋₈ alkyl, and R⁴ is H or C₁₋₈ alkyl. -   [28] A sulfamoyl compound described in [1] above, in which R¹ and R²     are Me, Y is H, W is a chemical bond, A is A-1, D, E, F and G are     CR⁷, CR⁸, CR⁹ or CR¹⁰, R³ is C₁₋₈ haloalkyl, and R⁴ is H, halogen or     C₁₋₈ alkyl. -   [29] A sulfamoyl compound described in [1] above, in which R¹ and R²     are Me, Y is H, W is a chemical bond, A is A-1, D, E, F and G are     CR⁷, CR⁸, CR⁹ or CR¹⁰, R³ is H or C₁₋₈ alkyl, and R⁴ is C₁₋₆     alkoxycarbonyl. -   [30] A sulfamoyl compound described in [1] above, in which R¹ and R²     are Me, Y is H, W is a chemical bond, A is A-1, D, E, F and G are     CR⁷, CR⁸, CR⁹ or CR¹⁰, R³ is H, and R⁴ is halogen. -   [31] A sulfamoyl compound described in [1] above, in which R¹ and R²     are Me, Y is H, W is a chemical bond, A is A-1, D, E, F and G are     CR⁷, CR⁸, CR⁹, or CR¹⁰, R³ is CN, and R⁴ is H or C₁₋₈ alkyl. -   [32] A sulfamoyl compound described in [1] above, in which R¹ and R²     are Me, Y is H, W is a chemical bond, A is A-1, any of D, E, F and G     is CH, R³ is C₁₋₈, alkyl, and R⁴ is halogen. -   [33] A sulfamoyl compound described in [1] above, in which R¹ and R²     are Me, Y is H, W is a chemical bond, A is A-1, any of D, E, F and G     is CH, and any of R³ and R⁴ is halogen. -   [34] A sulfamoyl compound described in [1] above, in which R¹ and R²     are Me, Y is H, W is a chemical bond, A is A-1, any of D, E, F and G     is CH, R³ is C₁₋₈ haloalkyl, and R⁴ is H or C₁₋₃ alkyl. -   [35] A sulfamoyl compound described in [1] above, in which R¹ and R²     are Me, Y is H, W is a chemical bond, A is A-1, any of D, E, F and G     is CH, R³ is Me or Et, and R⁴ is Cl or Br. -   [36] A sulfamoyl compound described in [1] above, in which R¹ and R²     are Me, Y is H, W is a chemical bond, A is A-1, any of D, E, F and G     is CH, R³ is Cl or Br, and R⁴ is Cl or Br. -   [37] An agricultural chemical containing as the active ingredient at     least one sulfamoyl compound described in [1] to [36] above. -   [38] An agricultural chemical as described in [37] above, in which     the agricultural chemical is an agricultural and horticultural     fungicide.

In the compounds of the general formula (1), examples of C₁₋₄ alkyl for R¹ and R² are methyl, ethyl, n- or i-propyl, n-, i- or s-butyl and the like.

Examples of C₄₋₆, alkylene formed by R¹ and R² together are piperidine including the N to which R¹ and R² are bonded and the like.

Examples of C₄₋₆ alkyleneoxy formed by R¹ and R² together are morpholine including the N to which R¹ and R² are bonded and the like.

The definitions of substituents Y, R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰ and R¹¹ have following meanings.

Examples of C₁₋₈ alkyl are methyl, ethyl, n- or i-propyl, n- or i-butyl, n-pentyl and the like.

Examples of C₃₋₈ cycloalkyl are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like.

Examples of C₂₋₈ alkenyl are allyl, vinyl and the like.

Examples of C₅₋₈ cycloalkenyl are cyclopentenyl and the like.

Examples of C₂₋₈ alkynyl are propargyl and the like.

Examples of C₁₋₈ alkoxy are methoxy, ethoxy and the like.

Examples of C₃₋₈ cycloalkyloxy are cyclopropyloxy and the like.

Examples of C₃₋₈ cycloalkenyloxy are cyclopentenyl-3-oxy and the like.

Examples of C₂₋₈ alkenyloxy are allyloxy and the like.

Examples of C₂₋₈ alkynyloxy are propargyloxy and the like.

Examples of C₁₋₈ alkylthio are methylthio, ethylthio, n- or i-propylthio and the like.

Examples of C₃₋₈ cycloalkylthio are cyclopentylthio and the like.

Examples of C₃₋₈ cycloalkenylthio are cyclopentenyl-3-thio and the like.

Examples of C₂₋₈ alkenylthio are allylthio and the like.

Examples of C₂₋₈ alkynylthio are propargylthio and the like.

Examples of C₁₋₈ haloalkoxy are trifluoromethoxy and the like.

Examples of C₁₋₈ haloalkylthio are trifluoromethylthio and the like.

Examples of C₁₋₈ haloalkyl are chloromethyl, dichloromethyl, dichlorofluoromethyl, trifluoromethyl and the like.

Examples of C₂₋₈ haloalkenyl are 3-chloroallyl and the like.

Examples of C₂₋₈ haloalkenyloxy are 3-chloroallyloxy and the like.

Examples of C₂₋₈ haloalkenylthio are 3-chloroallylthio and the like.

Examples of C₂₋₈ haloalkynyl are iodopropargyl and the like.

Examples of C₂₋₈ haloalkynyloxy are iodopropargyloxy and the like.

Examples of C₂₋₈ haloalkynylthio are iodopropargylthio and the like.

Examples of C₁₋₈ hydroxyalkyl are hydroxymethyl, 1-hydroxyethyl and the like.

Examples of C₁₋₈ hydroxyhaloalkyl are 2,2,2-trifluoro-1-hydroxyethyl and the like.

Examples of C₁₋₆ alkoxy C₁₋₄ alkyl are methoxymethyl, methoxyethyl and the like.

Examples of C₁₋₆ haloalkoxy C₁₋₄ alkyl are trifluoroethoxymethyl and the like.

Examples of C₁₋₆ alkylthio C₁₋₄ alkyl are methylthiomethyl, ethylthiomethyl, methylthioethyl and the like.

Examples of C₁₋₆ haloalkylthio C₁₋₄ alkyl are trifluoroethylthiomethyl and the like.

Examples of C₁₋₁₀ dialkoxy C₁₋₄ alkyl are dimethoxymethyl, diethoxymethyl and the like.

Examples of C₁₋₁₀ dialkylthio C₁₋₄ alkyl are dimethylthiomethyl, diethylthiomethyl and the like.

Examples of C₁₋₃ alkylenedioxy C₁₋₄ alkyl are ethylenedioxymethyl and the like.

Examples of C₁₋₃ alkylenedithio C₁₋₄ alkyl are ethylenedithiomethyl and the like.

Examples of phenoxy C₁₋₄ alkyl which may be substituted are phenoxymethyl and the like.

Examples of phenoxy which may be substituted are phenoxy and the like.

Examples of phenylthio C₁₋₄ alkyl which may be substituted are phenylthiomethyl and the like.

Examples of phenylthio which may be substituted are phenylthlo and the like.

Examples of phenyl C₁₋₄ alkyl which may be substituted are benzyl, phenethyl and the like.

Examples of benzylthio which may be substituted are benzylthio and the like.

Examples of benzyloxy which may be substituted are benzyloxy and the like.

Examples of phenyl which may be substituted are phenyl and the like.

Examples of benzoyl which may be substituted are benzoyl and the like.

Examples of benzoyl C₁₋₄ alkyl which may be substituted are benzoylmethyl and the like.

Examples of benzoyloxy which may be substituted are benzoyloxy and the like.

Examples of benzoyloxy C₁₋₄ alkyl which may be substituted are benzoyloxymethyl and the like.

Examples of naphthyl which may be substituted are naphthyl and the like.

Examples of 5- or 6-membered heterocyclic ring are pyridine, thiophene, furan, thiazole and the like.

Examples of C₁₋₆ alkoxycarbonyl are methoxycarbonyl and the like.

Examples of C₁₋₆ alkoxycarbonyl C₁₋₄ alkyl are methoxycarbonylmethyl and the like.

Examples of C₁₋₆ haloalkoxycarbonyl are fluoroethoxycarbonyl and the like.

Examples of C₁₋₆ haloalkoxycarbonyl C₁₋₄ alkyl are fluoroethoxycarbonylmethyl and the like.

Examples of C₁₋₆ alkoxyoxalyl are methoxyoxalyl, ethoxyoxalyl and the like.

Examples of C₁₋₆ dialkylamino are dimethylamino and the like.

Examples of C₁₋₆ alkylamino are methylamino and the like.

Examples of C₁₋₆ dialkylamino C₁₋₄ alkyl are dimethylaminomethyl and the like.

Examples of C₂₋₆ alkyleneimino are pyrrolidino, piperidino and the like.

Examples of C₂₋₆ alkyleneiminocarbonyl are pyrrolidinocarbonyl, piperidinocarbonyl and the like.

Examples of C₂₋₆ alkyleneimlno C₁₋₄ alkyl are pyrrolidinomethyl, piperidinomethyl and the like.

Examples of C₂₋₆ alkyleneiminocarbonyl C₁₋₄ alkyl are pyrrolidinocarbonylmethyl, piperidinocarbonylmethyl and the like.

Examples of C₁₋₆ alkylcarbonylamino are acethylamino and the like.

Examples of C₁₋₆ alkoxycarbonylamino are methoxycarbonylamino and the like.

Examples of C₁₋₆ haloalkylcarbonylamino are trifluoroacethylamino and the like.

Examples of C₁₋₆ alkylsulfonylamino are methanesulfonylamino and the like.

Examples of C₁₋₆ haloalkylsulfonylamino are chloromethylsulfonylamino and the like.

Examples of C₁₋₆ alkylcarbonylamino C₁₋₄ alkyl are acetylaminomethyl and the like.

Examples of C₁₋₆ alkoxycarbonylamino C₁₋₄ alkyl are methoxycarbonylaminomethyl and the like.

Examples of C₁₋₆ haloalkylcarbonylamino C₁₋₄ alkyl are trifluoroacetylaminomethyl and the like.

Examples of C₁₋₆ alkylsulfonylamino C₁₋₄ alkyl are methanesulfonylaminomethyl and the like.

Examples of C₁₋₆ haloalkylsulfonylamino C₁₋₄ alkyl are chloromethylsulfonylaminomethyl and the like.

Examples of C₁₋₆ dialkylaminocarbonyl are dimethylaminocarbonyl and the like.

Examples of C₁₋₆ dialkylaminocarbonyl C₁₋₄ alkyl are dimethylaminocarbonylmethyl and the like.

Examples of C₁₋₆ alkylcarbonyl are acetyl and the like.

Examples of C₁₋₆ haloalkylcarbonyl are trifluoroacetyl and the like.

Examples of C₁₋₆ alkylcarbonyloxy are acetyloxy and the like.

Examples of C₁₋₆ haloalkylcarbonyloxy are trifluoroacetyloxy and the like.

Examples of C₁₋₆ alkylcarbonyl C₁₋₄ alkyl are acetylmethyl and the like.

Examples of C₁₋₆ haloalkylcarbonyl C₁₋₄ alkyl are trifluoroacetylmethyl and the like.

Examples of C₁₋₆ alkylcarbonyloxy C₁₋₄ alkyl are acetyloxymethyl and the like.

Examples of C₁₋₆ haloalkylcarbonyloxy C₁₋₄ alkyl are trifluoroacetyloxymethyl and the like.

Examples of hydroxyimino C₁₋₄ alkyl are hydroxyiminomethyl and the like.

Examples of alkoxyimino C₁₋₄ alkyl are methoxyiminomethyl and the like.

Examples of C₁₋₆ alkylcarbonyloxyimino C₁₋₄ alkyl are acetyloxyiminomethyl and the like.

Examples of C₁₋₆ alkylsulfonyloxyimino C₁₋₄ alkyl are methanesulfonyloxyiminomethyl and the like.

Examples of C₁₋₆ alkylsulfoxy are methylsulfoxy and the like.

Examples of C₁₋₆ alkylsulfoxy C₁₋₄ alkyl are methylsulfoxymethyl, ethylsulfoxymethyl, methylsulfoxyethyl and the like.

Examples of C₁₋₆ alkylsulfonyl are methanesulfonyl and the like.

Examples of C₁₋₆ alkylsulfonyloxy are methanesulfonyloxy and the like.

Examples of C₁₋₆ alkylsulfonyl C₁₋₄ alkyl are methylsulfonylmethyl, ethylsulfonylmethyl, methylsulfonylethyl and the like.

Examples of C₁₋₆ alkylsulfonyloxy C₁₋₄ alkyl are methylsulfonyloxymethyl and the like.

Examples of C₁₋₆ haloalkylsulfoxy are chloromethylsulfoxy and the like.

Examples of C₁₋₆ haloalkylsulfoxy C₁₋₄ alkyl are chloromethylsulfoxymethyl and the like.

Examples of C₁₋₆ haloalkylsulfonyl are trifluoromethylsulfonyl and the like.

Examples of C₁₋₆ haloalkylsulfonyloxy are trifluoromethylsulfonyloxy and the like.

Examples of C₁₋₆ haloalkylsulfonyl C₁₋₄ alkyl are trifluoromethylsulfonylmethyl and the like.

Examples of C₁₋₆ haloalkylsulfonyloxy C₁₋₄ alkyl are trifluoromethylsulfonyloxymethyl and the like.

Examples of C₁₋₆ dialkylsulfamoyl are dimethylsulfamoyl and the like.

Examples of C₁₋₆ dialkylsulfamoyl C₁₋₄ alkyl are dimethylsulfamoylmethyl and the like.

Examples of C₁₋₆ alkoxysulfonyl are methoxysulfonyl and the like.

Examples of C₁₋₆ alkoxysulfonyl C₁₋₄ alkyl are methoxysulfonylmethyl and the like.

Examples of C₁₋₆ haloalkoxysulfonyl are fluoroethoxysulfonyl and the like.

Examples of C₁₋₆ haloalkoxysulfonyl C₁₋₄ alkyl are fluoroethoxysulfonylmethyl and the like.

Examples of C₁₋₆ nitroalkyl are nitromethyl and the like.

Examples of C₂₋₆ cyanoalkyl are cyanomethyl and the like.

Examples of C₁₋₆ thiocarbamoyl are CSNH₂ and the like.

Examples of halogen are F, Cl, Br and I.

Examples of C₁₋₃ alkylenedioxy which may be substituted with halogen are difluoromethylenedioxy, tetrafluoroethylenedioxy and the like.

Next, the compounds of the invention of the formula (1) are shown in Tables 1 to 11. However, the present invention should not be construed as being limited thereto.

In the Tables, Me denotes methyl, Et denotes ethyl, Pr denotes propyl, Bu denotes butyl, n- denotes normal, i- denotes iso, s- denotes secondary, t- denotes tertiary, Ph denotes phenyl, Bn denotes benzyl, and Ac denotes acetyl.

TABLE 1

Compound No. R³ R⁴ 1-1 H H 1-2 Me H 1-3 Et H 1-4 n-Pr H 1-5 i-Pr H 1-6 n-Bu H 1-7 Ph H 1-8 Bn H 1-9 F H 1-10 Cl H 1-11 Br H 1-12 I H 1-13 SMe H 1-14 SEt H 1-15 CH₂OMe H 1-16 CClF₂ H 1-17 CHF₂ H 1-18 CHFCl H 1-19 CH₂Cl H 1-20 CF₃ H 1-21 CN H 1-22 CHO H 1-23 C₂F₅ H 1-24 CH═NOMe H 1-25 CO₂Me H 1-26 CO₂Et H 1-27 CONMe₂ H 1-28 COMe H 1-29 COPh H 1-30 CH₂CO₂Me H 1-31 NO₂ H 1-32 H Cl 1-33 Me Cl 1-34 Et Cl 1-35 n-Pr Cl 1-36 i-Pr Cl 1-37 n-Bu Cl 1-38 Ph Cl 1-39 Bn Cl 1-40 F Cl 1-41 Cl Cl 1-42 Br Cl 1-43 I Cl 1-44 SMe Cl 1-45 SEt Cl 1-46 CH₂OMe Cl 1-47 CHF₂ Cl 1-48 CHFCl Cl 1-49 CH₂Cl Cl 1-50 CF₃ Cl 1-51 CN Cl 1-52 CHO Cl 1-53 C₂F₅ Cl 1-54 CH═NOMe Cl 1-55 CO₂Me Cl 1-56 CO₂Et Cl 1-57 CONMe₂ Cl 1-58 COMe Cl 1-59 CClF₂ Cl 1-60 CH₂CO₂Me Cl 1-61 NO₂ Cl 1-62 H Br 1-63 Me Br 1-64 Et Br 1-65 n-Pr Br 1-66 i-Pr Br 1-67 n-Bu Br 1-68 Ph Br 1-69 Bn Br 1-70 F Br 1-71 Cl Br 1-72 Br Br 1-73 I Br 1-74 SMe Br 1-75 SEt Br 1-76 CH₂OMe Br 1-77 CHF₂ Br 1-78 CHFCl Br 1-79 CH₂Cl Br 1-80 CF₃ Br 1-81 CN Br 1-82 CHO Br 1-83 C₂F₅ Br 1-84 CH═NOMe Br 1-85 CO₂Me Br 1-86 CO₂Et Br 1-87 CONMe₂ Br 1-88 COMe Br 1-89 CClF₂ Br 1-90 CH₂CO₂Me Br 1-91 NO₂ Br 1-92 H I 1-93 Me I 1-94 Et I 1-95 n-Pr I 1-96 n-Bu I 1-97 Ph I 1-98 F I 1-99 Cl I 1-100 Br I 1-101 I I 1-102 SMe I 1-103 CF₃ I 1-104 CN I 1-105 H F 1-106 Me F 1-107 Et F 1-108 n-Pr F 1-109 n-Bu F 1-110 Ph F 1-111 F F 1-112 Cl F 1-113 Br F 1-114 CO₂Et F 1-115 SMe F 1-116 CF₃ F 1-117 CN F 1-118 H Me 1-119 Me Me 1-120 Et Me 1-121 n-Pr Me 1-122 CF₂Cl Me 1-123 CHF₂ Me 1-124 F Me 1-125 Cl Me 1-126 Br Me 1-127 I Me 1-128 SMe Me 1-129 CF₃ Me 1-130 CN Me 1-131 CHO Me 1-132 CH═NOH Me 1-133 CH═NOMe Me 1-134 CH═NOAc Me 1-135 H Et 1-136 Me Et 1-137 Et Et 1-138 n-Pr Et 1-139 F Et 1-140 Cl Et 1-141 Br Et 1-142 CHF₂ Et 1-143 CClF₂ Et 1-144 CF₃ Et 1-145 CN Et 1-146 CHO Et 1-147 —(CH₂)₃— 1-148 —(CH₂)₄— 1-149 —(CH₂)₅— 1-150 —(CH₂)₆— 1-151 H Ph 1-152 Me Ph 1-153 Et Ph 1-154 n-Pr Ph 1-155 F Ph 1-156 Cl Ph 1-157 Br Ph 1-158 I Ph 1-159 SMe Ph 1-160 CF₃ Ph 1-161 CN Ph 1-162 CHO Ph 1-163 H Bn 1-164 Me Bn 1-165 Et Bn 1-166 n-Pr Bn 1-167 F Bn 1-168 Cl Bn 1-169 Br Bn 1-170 I Bn 1-171 SMe Bn 1-172 CF₃ Bn 1-173 CN Bn 1-174 H CF₃ 1-175 Me CF₃ 1-176 Et CF₃ 1-177 n-Pr CF₃ 1-178 n-Bu CF₃ 1-179 Ph CF₃ 1-180 F CF₃ 1-181 Cl CF₃ 1-182 Br CF₃ 1-183 I CF₃ 1-184 SMe CF₃ 1-185 CF₃ CF₃ 1-186 CN CF₃ 1-187 H CHO 1-188 Me CHO 1-189 Et CHO 1-190 n-Pr CHO 1-191 n-Bu CHO 1-192 F CHO 1-193 Cl CHO 1-194 Br CHO 1-195 I CHO 1-196 SMe CHO 1-197 CF₃ CHO 1-198 CN CHO 1-199 H CH═NOH 1-200 Me CH═NOH 1-201 Et CH═NOH 1-202 n-Pr CH═NOH 1-203 F CH═NOH 1-204 Cl CH═NOH 1-205 Br CH═NOH 1-206 I CH═NOH 1-207 SMe CH═NOH 1-208 CF₃ CH═NOH 1-209 CN CH═NOH 1-210 H CH═NOMe 1-211 Me CH═NOMe 1-212 Et CH═NOMe 1-213 n-Pr CH═NOMe 1-214 F CH═NOMe 1-215 Cl CH═NOMe 1-216 Br CH═NOMe 1-217 I CH═NOMe 1-218 SMe CH═NOMe 1-219 CF₃ CH═NOMe 1-220 CN CH═NOMe 1-221 H CH═NOAc 1-222 Me CH═NOAc 1-223 Et CH═NOAc 1-224 n-Pr CH═NOAc 1-225 F CH═NOAc 1-226 Cl CH═NOAc 1-227 Br CH═NOAc 1-228 I CH═NOAc 1-229 SMe CH═NOAc 1-230 CF₃ CH═NOAc 1-231 CN CH═NOAc 1-232 H COMe 1-233 Me COMe 1-234 Et COMe 1-235 n-Pr COMe 1-236 n-Bu COMe 1-237 F COMe 1-238 Cl COMe 1-239 Br COMe 1-240 I COMe 1-241 SMe COMe 1-242 CF₃ COMe 1-243 CN COMe 1-244 H COEt 1-245 Me COEt 1-246 Et COEt 1-247 n-Pr COEt 1-248 n-Bu COEt 1-249 Ph COEt 1-250 F COEt 1-251 Cl COEt 1-252 Br COEt 1-253 I COEt 1-254 SMe COEt 1-255 CF₃ COEt 1-256 CN COEt 1-257 H COPh 1-258 Me COPh 1-259 Et COPh 1-260 n-Pr COPh 1-261 F COPh 1-262 Cl COPh 1-263 Br COPh 1-264 I COPh 1-265 H COCF₃ 1-266 Me COCF₃ 1-267 Et COCF₃ 1-268 n-Pr COCF₃ 1-269 F COCF₃ 1-270 Cl COCF₃ 1-271 Br COCF₃ 1-272 I COCF₃ 1-273 SMe COCF₃ 1-274 CF₃ COCF₃ 1-275 CM COCF₃ 1-276 H CO₂Me 1-277 Me CO₂Me 1-278 Et CO₂Me 1-279 n-Pr CO₂Me 1-280 n-Bu CO₂Me 1-281 Ph CO₂Me 1-282 F CO₂Me 1-283 Cl CO₂Me 1-284 Br CO₂Me 1-285 I CO₂Me 1-286 SMe CO₂Me 1-287 CF₃ CO₂Me 1-288 CM CO₂Me 1-289 H CO₂Et 1-290 Me CO₂Et 1-291 Et CO₂Et 1-292 F CO₂Et 1-293 Cl CO₂Et 1-294 Br CO₂Et 1-295 SMe CO₂Et 1-296 CF₃ CO₂Et 1-297 CM CO₂Et 1-298 H CO₂n-Pr 1-299 Me CO₂n-Pr 1-300 Et CO₂n-Pr 1-301 F CO₂n-Pr 1-302 Cl CO₂n-Pr 1-303 Br CO₂n-Pr 1-304 SMe CO₂n-Pr 1-305 CF₃ CO₂n-Pr 1-306 CN CO₂n-Pr 1-307 H CO₂I-Pr 1-309 Et CO₂I-Pr 1-310 F CO₂I-Pr 1-311 Cl CO₂I-Pr 1-312 Br CO₂I-Pr 1-313 SMe CO₂I-Pr 1-314 CF₃ CO₂I-Pr 1-315 CN CO₂I-Pr 1-316 H CO₂n-Bu 1-317 Me CO₂n-Bu 1-318 Et CO₂n-Bu 1-319 F CO₂n-Bu 1-320 Cl CO₂n-Bu 1-321 Br CO₂n-Bu 1-322 SMe CO₂n-Bu 1-323 CF₃ CO₂n-Bu 1-324 CN CO₂n-Bu 1-325 H CO₂I-Bu 1-326 Me CO₂I-Bu 1-327 Et CO₂I-Bu 1-328 F CO₂I-Bu 1-329 Cl CO₂I-Bu 1-330 Br CO₂I-Bu 1-331 SMe CO₂I-Bu 1-332 CF₃ CO₂I-Bu 1-333 CN CO₂I-Bu 1-334 H CO₂s-Bu 1-335 Me CO₂s-Bu 1-336 Et CO₂s-Bu 1-337 F CO₂s-Bu 1-338 Cl CO₂s-Bu 1-339 Br CO₂s-Bu 1-340 SMe CO₂s-Bu 1-341 CF₃ CO₂s-Bu 1-342 CN CO₂s-Bu 1-343 H CO₂t-Bu 1-344 Me CO₂t-Bu 1-345 Et CO₂t-Bu 1-346 F CO₂t-Bu 1-347 Cl CO₂t-Bu 1-348 Br CO₂t-Bu 1-349 SMe CO₂t-Bu 1-350 CF₃ CO₂t-Bu 1-351 CN CO₂t-Bu 1-352 H CO₂Ph 1-353 Me CO₂Ph 1-354 Et CO₂Ph 1-355 F CO₂Ph 1-356 Cl CO₂Ph 1-357 Br CO₂Ph 1-358 SMe CO₂Ph 1-359 CF₃ CO₂Ph 1-360 CN CO₂Ph 1-361 H COCO₂Me 1-362 Me COCO₂Me 1-363 F COCO₂Me 1-364 Cl COCO₂Me 1-365 Br COCO₂Me 1-366 SMe COCO₂Me 1-367 CF₃ COCO₂Me 1-368 CN COCO₂Me 1-369 H COCO₂Et 1-370 Me COCO₂Et 1-371 F COCO₂Et 1-372 Cl COCO₂Et 1-373 Br COCO₂Et 1-374 SMe COCO₂Et 1-375 CF₃ COCO₂Et 1-376 CN COCO₂Et 1-377 H SMe 1-378 Me SMe 1-379 Et SMe 1-380 n-Pr SMe 1-381 F SMe 1-382 Cl SMe 1-383 Br SMe 1-384 I SMe 1-385 SMe SMe 1-386 CF₃ SMe 1-387 CN SMe 1-388 H SOMe 1-389 Me SOMe 1-390 Et SOMe 1-391 Cl SOMe 1-392 Br SOMe 1-393 CF₃ SOMe 1-394 CN SOMe 1-395 H SO₂Me 1-396 Me SO₂Me 1-397 Et SO₂Me 1-398 Cl SO₂Me 1-399 Br SO₂Me 1-400 CF₃ SO₂Me 1-401 CN SO₂Me 1-402 H SPh 1-403 Me SPh 1-404 Et SPh 1-405 n-Pr SPh 1-406 F SPh 1-407 Cl SPh 1-408 Br SPh 1-409 I SPh 1-410 SHe SPh 1-411 CF₃ SPh 1-412 CN SPh 1-413 H SOPh 1-414 Me SOPh 1-415 Et SOPh 1-416 Cl SOPh 1-417 Br SOPh 1-418 CF₃ SOPh 1-419 CN SOPh 1-420 H SO₂Ph 1-421 Me SO₂Ph 1-422 Et SO₂Ph 1-423 Cl SO₂Ph 1-424 Br SO₂Ph 1-425 CF₃ SO₂Ph 1-426 CN SO₂Ph 1-427 H NO₂ 1-428 Me NO₂ 1-429 Et NO₂ 1-430 Cl NO₂ 1-431 Br NO₂ 1-432 SMe NO₂ 1-433 CF₃ NO₂ 1-434 CN NO₂ 1-435 H CN 1-436 Me CN 1-437 Et CN 1-438 n-Pr CN 1-439 F CN 1-440 Cl CN 1-441 Br CN 1-442 SMe CN 1-443 CF₃ CN 1-444 CN CN 1-445 H CH₂CN 1-446 Me CH₂CN 1-447 Et CH₂CN 1-448 n-Pr CH₂CN 1-449 Cl CH₂CN 1-450 Br CH₂CN 1-451 SMe CH₂CN 1-452 CF₃ CH₂CN 1-453 CN CH₂CN 1-454 H OMe 1-455 Me OMe 1-456 Et OMe 1-457 Cl OMe 1-458 Br OMe 1-459 SMe OMe 1-460 CF₃ OMe 1-461 CN OMe 1-462 H CH₂NMe₂ 1-463 Me CH₂NMe₂ 1-464 Et CH₂NMe₂ 1-465 Cl CH₂NMe₂ 1-466 Br CH₂NMe₂ 1-467 SMe CH₂NMe₂ 1-468 CF₃ CH₂NMe₂ 1-469 CN CH₂NMe₂ 1-470 H OCOMe 1-471 Me OCOMe 1-472 Et OCOMe 1-473 Cl OCOMe 1-474 Br OCOMe 1-475 SMe OCOMe 1-476 CF₃ OCOMe 1-477 CN OCOMe 1-478 H CH(OMe)₂ 1-479 Me CH(OMe)₂ 1-480 Et CH(OMe)₂ 1-481 n-Pr CH(OMe)₂ 1-482 Cl CH(OMe)₂ 1-483 Br CH(OMe)₂ 1-484 SMe CH(OMe)₂ 1-485 CF₃ CH(OMe)₂ 1-486 CN CH(OMe)₂ 1-487 H CH(SMe)₂ 1-488 Me CH(SMe)₂ 1-489 Et CH(SMe)₂ 1-490 n-Pr CH(SMe)₂ 1-491 Cl CH(SMe)₂ 1-492 Br CH(SMe)₂ 1-493 SMe CH(SMe)₂ 1-494 CF₃ CH(SMe)₂ 1-495 CN CH(SMe)₂ 1-496 H CH₂Cl 1-497 Me CH₂Cl 1-498 Et CH₂Cl 1-499 n-Pr CH₂Cl 1-500 F CH₂Cl 1-501 Cl CH₂Cl 1-502 Br CH₂Cl 1-503 I CH₂Cl 1-504 SMe CH₂Cl 1-505 CF₃ CH₂Cl 1-506 CN CH₂Cl 1-507 H CH₂OH 1-508 Me CH₂OH 1-509 Et CH₂OH 1-510 n-Pr CH₂OH 1-511 F CH₂OH 1-512 Cl CH₂OH 1-513 Br CH₂OH 1-514 SMe CH₂OH 1-515 CF₃ CH₂OH 1-516 CN CH₂OH 1-517 H CH(OH)Me 1-518 Me CH(OH)Me 1-519 Et CH(OH)Me 1-520 n-Pr CH(OH)Me 1-521 F CH(OH)Me 1-522 Cl CH(OH)Me 1-523 Br CH(OH)Me 1-524 SMe CH(OH)Me 1-525 CF₃ CH(OH)Me 1-526 CN CH(OH)Me 1-527 H CH(OH)Et 1-528 Me CH(OH)Et 1-529 Et CH(OH)Et 1-530 n-Pr CH(OH)Et 1-531 F CH(OH)Et 1-532 Cl CH(OH)Et 1-533 Br CH(OH)Et 1-534 SM CH(OH)Et 1-535 CF₃ CH(OH)Et 1-536 CN CH(OH)Et 1-537 H CH(OH)CF₃ 1-538 Me CH(OH)CF₃ 1-539 Et CH(OH)CF₃ 1-540 n-Pr CH(OH)CF₃ 1-541 F CH(OH)CF₃ 1-542 Cl CH(OH)CF₃ 1-543 Br CH(OH)CF₃ 1-544 SMe CH(OH)CF₃ 1-545 CF₃ CH(OH)CF₃ 1-546 CN CH(OH)CF₃ 1-547 H CH₂OMe 1-548 Me CH₂OMe 1-549 Et CH₂OMe 1-550 n-Pr CH₂OMe 1-551 F CH₂OMe 1-552 Cl CH₂OMe 1-553 Br CH₂OMe 1-554 SMe CH₂OMe 1-555 CF₃ CH₂OMe 1-556 CN CH₂OMe 1-557 H CONMe₂ 1-558 Me CONMe₂ 1-559 Et CONMe₂ 1-560 n-Pr CONMe₂ 1-561 F CONMe₂ 1-562 Cl CONMe₂ 1-563 Br CONMe₂ 1-564 SMe CONMe₂ 1-565 CF₃ CONMe₂ 1-566 CN CONMe₂ 1-567 H CO(4-CF₃Ph) 1-568 Me CO(4-CF₃Ph) 1-569 Et CO(4-CF₃Ph) 1-570 Cl CO(4-CF₃Ph) 1-571 Br CO(4-CF₃Ph)

TABLE 2

Compound No. R⁷ R⁸ R⁹ R¹⁰ 2-1 F H H H 2-2 H F H H 2-3 H H F H 2-4 H H H F 2-5 Cl H H H 2-6 H Cl H H 2-7 H H Cl H 2-8 H H H Cl 2-9 Br H H H 2-10 H Br H H 2-11 H H Br H 2-12 H H H Br 2-13 I H H H 2-14 H I H H 2-15 H H I H 2-16 H H H I 2-17 Me H H H 2-18 H Me H H 2-19 H H Me H 2-20 H H H Me 2-21 Et H H H 2-22 H Et H H 2-23 H H Et H 2-24 H H H Et 2-25 MeO H H H 2-26 H MeO H H 2-27 H H MeO H 2-28 H H H MeO 2-29 NO₂ H H H 2-30 H NO₂ H H 2-31 H H NO₂ H 2-32 H H H NO₂ 2-33 CN H H H 2-34 H CN H H 2-35 H H CN H 2-36 H H H CN 2-37 CF₃ H H H 2-38 H CF₃ H H 2-39 H H CF₃ H 2-40 H H H CF₃ 2-41 CO₂Me H H H 2-42 H CO₂Me H H 2-43 H H CO₂Me H 2-44 H H H CO₂Me

TABLE 3

Compound No. R⁷ R⁸ R⁹ R¹⁰ 3-1 H H H H 3-2 F H H H 3-3 H F H H 3-4 H H F H 3-5 H H H F 3-6 Cl H H H 3-7 H Cl H H 3-8 H H Cl H 3-9 H H H Cl 3-10 Br H H H 3-11 H Br H H 3-12 H H Br H 3-13 H H H Br 3-14 Me H H H 3-15 H Me H H 3-16 H H Me H 3-17 H H H Me 3-18 CF₃ H H H 3-19 H CF₃ H H 3-20 H H CF₃ H 3-21 H H H CF₃

TABLE 4

Compound No. R³ R⁴ 4-1 H H 4-2 H Me 4-3 H Et 4-4 H Cl 4-5 H Br 4-6 H CF₃ 4-7 Me H 4-8 Me Me 4-9 Me Et 4-10 Me Cl 4-11 Me Br 4-12 Me CF₃ 4-13 Et H 4-14 Et Me 4-15 Et Et 4-16 Et Cl 4-17 Et Br 4-18 Et CF₃ 4-19 Cl H 4-20 Cl Me 4-21 Cl Et 4-22 Cl Cl 4-23 Cl Br 4-24 Cl CF₃ 4-25 Br H 4-26 Br Me 4-27 Br Et 4-28 Br Br 4-29 Br CF₃

TABLE 5

Compound No. R³ R⁴ R⁵ R⁶ 5-1 H Ph H H 5-2 Cl Ph H H 5-3 H Ph Cl H 5-4 H Ph H Cl 5-5 Cl Ph Cl H 5-6 Cl Ph H Cl 5-7 H Ph Cl Cl 5-8 Cl Ph Cl Cl 5-9 Br Ph Cl H 5-10 Cl Ph Br H 5-11 Br Ph H Cl 5-12 Cl Ph H Br 5-13 H Ph Br Cl 5-14 H Ph Cl Br 5-15 Br Ph Cl Cl 5-16 Cl Ph Br Cl 5-17 Cl Ph Cl Br 5-18 Br Ph Br Cl 5-19 Br Ph Cl Br 5-20 Cl Ph Br Br 5-21 Me Ph H H 5-22 H Ph Me H 5-23 H Ph H Me 5-24 Me Ph Cl H 5-25 Me Ph H Cl 5-26 Me Ph Cl Cl 5-27 Me Ph Br Cl 5-28 Me Ph Cl Br 5-29 Cl Ph Me H 5-30 H Ph Me Cl 5-31 Cl Ph Me Cl 5-32 Br Ph Me Cl 5-33 Cl Ph Me Br 5-34 Cl Ph H Me 5-35 H Ph Cl Me 5-36 Cl Ph Cl Me 5-37 Br Ph Cl Me 5-38 Cl Ph Br Me 5-39 Br Ph H H 5-40 H Ph Br H 5-41 H Ph H Br 5-42 Br Ph Br H 5-43 Br Ph H Br 5-44 H Ph Br Br 5-45 Br Ph Br Br 5-46 Me Ph Br H 5-47 Me Ph H Br 5-48 Me Ph Br Br 5-49 Br Ph Me H 5-50 H Ph Me Br 5-51 Br Ph Me Br 5-52 Br Ph H Me 5-53 H Ph Br Me 5-54 Br Ph Br Me 5-55 Me Ph Me H 5-56 Me Ph Me Cl 5-57 Me Ph Me Br 5-58 H Ph Me Me 5-59 Cl Ph Me Me 5-60 Br Ph Me Me 5-61 Me Ph H Me 5-62 Me Ph Cl Me 5-63 Me Ph Br Me 5-64 CO₂Me Ph Me H 5-65 Me Ph CO₂Me H 5-66 CO₂Me Ph Me Cl 5-67 Me Ph CO₂Me Cl 5-68 CO₂Me Ph Me Br 5-69 Me Ph CO₂Me Br 5-70 Ac Ph Me H 5-71 Me Ph Ac H 5-72 Ac Ph Me Cl 5-73 Me Ph Ac Cl 5-74 Ac Ph Me Br 5-75 Me Ph Ac Br 5-76 CN Ph Me H 5-77 Me Ph CN H 5-78 CN Ph Me Cl 5-79 Me Ph CN Cl 5-80 CN Ph Me Br 5-81 Me Ph CN Br 5-82 H Ph CO₂Me Me 5-83 H Ph Me CO₂Me 5-84 Cl Ph CO₂Me Me 5-85 Cl Ph Me CO₂Me 5-86 Br Ph CO₂Me Me 5-87 Br Ph Me CO₂Me 5-88 H Ph Ac Me 5-89 H Ph Me Ac 5-90 Cl Ph Ac Me 5-91 Cl Ph Me Ac 5-92 Br Ph Ac Me 5-93 Br Ph Me Ac 5-94 H Ph CN Me 5-95 H Ph Me CN 5-96 Cl Ph CN Me 5-97 Cl Ph Me CN 5-98 Br Ph CN Me 5-99 Br Ph Me CN 5-100 CO₂Me Ph H Me 5-101 Me Ph H CO₂Me 5-102 CO₂Me Ph Cl Me 5-103 Me Ph Cl CO₂Me 5-104 CO₂Me Ph Br Me 5-105 Me Ph Br CO₂Me 5-106 Ac Ph H Me 5-107 Me Ph H Ac 5-108 Ac Ph Cl Me 5-109 Me Ph Cl Ac 5-110 Ac Ph Br Me 5-111 Me Ph Br Ac 5-112 CM Ph H Me 5-113 Me Ph H CN 5-114 CN Ph Cl Me 5-115 Me Ph Cl CN 5-116 CN Ph Br Me 5-117 Me Ph Br CM 5-118 Et Ph H H 5-119 H Ph Et H 5-120 H Ph H Et 5-121 Et Ph Cl H 5-122 Et Ph H Cl 5-123 Et Ph Cl Cl 5-124 Et Ph Br Cl 5-125 Et Ph Cl Br 5-126 Cl Ph Et H 5-127 H Ph Et Cl 5-128 Cl Ph Et Cl 5-129 Br Ph Et Cl 5-130 Cl Ph Et Br 5-131 Cl Ph H Et 5-132 H Ph Cl Et 5-133 Cl Ph Cl Et 5-134 Br Ph Cl Et 5-135 Cl Ph Br Et 5-136 Et Ph Br H 5-137 Et Ph H Br 5-138 Et Ph Br Br 5-139 Br Ph Et H 5-140 H Ph Et Br 5-141 Br Ph Et Br 5-142 Br Ph H Et 5-143 H Ph Br Et 5-144 Br Ph Br Et 5-145 CN Ph H H 5-146 H Ph CN H 5-147 H Ph H CN 5-148 CN Ph Cl H 5-149 CN Ph H Cl 5-150 CN Ph Cl Cl 5-151 CN Ph Br Cl 5-152 CN Ph Cl Br 5-153 Cl Ph CN H 5-154 H Ph CN Cl 5-155 Cl Ph CN Cl 5-156 Br Ph CN Cl 5-157 Cl Ph CN Br 5-158 Cl Ph H CN 5-159 H Ph Cl CN 5-160 Br Ph H CN 5-161 H Ph Br CN 5-162 CN Ph Br H 5-163 CN Ph H Br 5-164 CN Ph Br Br 5-165 Br Ph CN H 5-166 H Ph CN Br 5-167 Br Ph CN Br 5-168 Cl Ph Cl CN 5-169 Cl Ph Br CN 5-170 Br Ph Cl CN 5-171 Br Ph Br CN 5-172 CF₃ Ph H H 5-173 H Ph CF₃ H 5-174 H Ph H CF₃ 5-175 CF₃ Ph Cl H 5-176 CF₃ Ph H Cl 5-177 CF₃ Ph Cl Cl 5-178 CF₃ Ph Br Cl 5-179 CF₃ Ph Cl Br 5-180 Cl Ph CF₃ H 5-181 H Ph CF₃ Cl 5-182 Cl Ph CF₃ Cl 5-183 Br Ph CF₃ Cl 5-184 Cl Ph CF₃ Br 5-185 Cl Ph H CF₃ 5-186 H Ph Cl CF₃ 5-187 Cl Ph Cl CF₃ 5-188 Br Ph Cl CF₃ 5-189 Cl Ph Br CF₃ 5-190 CF₃ Ph Br H 5-191 CF₃ Ph H Br 5-192 CF₃ Ph Br Br 5-193 Br Ph CF₃ H 5-194 H Ph CF₃ Br 5-195 Br Ph CF₃ Br 5-196 Br Ph H CF₃ 5-197 H Ph Br CF₃ 5-198 Br Ph Br CF₃ 5-199 NO₂ Ph H H 5-200 H Ph NO₂ H 5-201 H Ph H NO₂ 5-202 NO₂ Ph Cl H 5-203 NO₂ Ph H Cl 5-204 NO₂ Ph Cl Cl 5-205 NO₂ Ph Br Cl 5-206 NO₂ Ph Cl Br 5-207 Cl Ph NO₂ H 5-208 H Ph NO₂ Cl 5-209 Cl Ph NO₂ Cl 5-210 Br Ph NO₂ Cl 5-211 Cl Ph NO₂ Br 5-212 Cl Ph H NO₂ 5-213 H Ph Cl NO₂ 5-214 Cl Ph Cl NO₂ 5-215 Br Ph Cl NO₂ 5-216 Cl Ph Br NO₂ 5-217 NO₂ Ph Br H 5-218 NO₂ Ph H Br 5-219 NO₂ Ph Br Br 5-220 Br Ph NO₂ H 5-221 H Ph NO₂ Br 5-222 Br Ph NO₂ Br 5-223 Br Ph H NO₂ 5-224 H Ph Br NO₂ 5-225 Br Ph Br NO₂ 5-226 CO₂Me Ph H H 5-227 H Ph CO₂Me H 5-228 H Ph H CO₂Me 5-229 CO₂Me Ph Cl H 5-230 CO₂Me Ph H Cl 5-231 CO₂Me Ph Cl Cl 5-232 CO₂Me Ph Br Cl 5-233 CO₂Me Ph Cl Br 5-234 Cl Ph CO₂Me H 5-235 H Ph CO₂Me Cl 5-236 Cl Ph CO₂Me Cl 5-237 Br Ph CO₂Me Cl 5-238 Cl Ph CO₂Me Br 5-239 Cl Ph H CO₂Me 5-240 H Ph Cl CO₂Me 5-241 Cl Ph Cl CO₂Me 5-242 Br Ph Cl CO₂Me 5-243 Cl Ph Br CO₂Me 5-244 CO₂Me Ph Br H 5-245 CO₂Me Ph H Br 5-246 CO₂Me Ph Br Br 5-247 Br Ph CO₂Me H 5-248 H Ph CO₂Me Br 5-249 Br Ph CO₂Me Br 5-250 Br Ph H CO₂Me 5-251 H Ph Br CO₂Me 5-252 Br Ph Br CO₂Me 5-253 Ac Ph H H 5-254 H Ph Ac H 5-255 H Ph H Ac 5-256 Ac Ph Cl H 5-257 Ac Ph H Cl 5-258 Ac Ph Cl Cl 5-259 Ac Ph Br Cl 5-260 Ac Ph Cl Br 5-261 Cl Ph Ac H 5-262 H Ph Ac Cl 5-263 Cl Ph Ac Cl 5-264 Br Ph Ac Cl 5-265 Cl Ph Ac Br 5-266 Cl Ph H Ac 5-267 H Ph Cl Ac 5-268 Cl Ph Cl Ac 5-269 Br Ph Cl Ac 5-270 Cl Ph Br Ac 5-271 Ac Ph Br H 5-272 Ac Ph H Br 5-273 Ac Ph Br Br 5-274 Br Ph Ac H 5-275 H Ph Ac Br 5-276 Br Ph Ac Br 5-277 Br Ph H Ac 5-278 H Ph Br Ac 5-279 Br Ph Br Ac 5-280 Ph H H H 5-281 Ph Cl H H 5-282 Ph H Cl H 5-283 Ph H H Cl 5-284 Ph Cl Cl H 5-285 Ph Br Cl H 5-286 Ph Cl Br H 5-287 Ph Cl H Cl 5-288 Ph Br H Cl 5-289 Ph Cl H Br 5-290 Ph H Cl Cl 5-291 Ph H Br Cl 5-292 Ph H Cl Br 5-293 Ph Cl Cl Cl 5-294 Ph Br Cl Cl 5-295 Ph Cl Br Cl 5-296 Ph Cl Cl Br 5-297 Ph Br Br Cl 5-298 Ph Br Cl Br 5-299 Ph Cl Br Br 5-300 Ph Me H H 5-301 Ph H Me H 5-302 Ph H H Me 5-303 Ph Me Cl H 5-304 Ph Me H Cl 5-305 Ph Me Cl Cl 5-306 Ph Me Br Cl 5-307 Ph Me Cl Br 5-308 Ph Cl Me H 5-309 Ph H Me Cl 5-310 Ph Cl Me Cl 5-311 Ph Cl Me Br 5-312 Ph Cl H Me 5-313 Ph H Cl Me 5-314 Ph Cl Cl Me 5-315 Ph Br H H 5-316 Ph H Br H 5-317 Ph H H Br 5-318 Ph Br Br H 5-319 Ph Br H Br 5-320 Ph H Br Br 5-321 Ph Br Br Br 5-322 Ph Me Br H 5-323 Ph Me H Br 5-324 Ph Me Br Br 5-325 Ph Br Me H 5-326 Ph H Me Br 5-327 Ph Br Me Br 5-328 Ph Br Me Cl 5-329 Ph Br H Me 5-330 Ph H Br Me 5-331 Ph Br Br Me 5-332 Ph CN H H 5-333 Ph H CN H 5-334 Ph H H CN 5-335 Ph CN Cl H 5-336 Ph CN H Cl 5-337 Ph CN Cl Cl 5-338 Ph CN Br Cl 5-339 Ph CN Cl Br 5-340 Ph Cl CN H 5-341 Ph H CN Cl 5-342 Ph Cl CN Cl 5-343 Ph Br CN Cl 5-344 Ph Cl CN Br 5-345 Ph Cl H CN 5-346 Ph H Cl CN 5-347 Ph Cl Cl CN 5-348 Ph Br Cl CN 5-349 Ph Cl Br CN 5-350 Ph CN Br H 5-351 Ph CN H Br 5-352 Ph CN Br Br 5-353 Ph Br CN H 5-354 Ph H CN Br 5-355 Ph Br CN Br 5-356 Ph Br H CN 5-357 Ph H Br CN 5-358 Ph Br Br CN 5-359 Ph CF₃ H H 5-360 Ph H CF₃ H 5-361 Ph H H CF₃ 5-362 Ph CF₃ Cl H 5-363 Ph CF₃ H Cl 5-364 Ph CF₃ Cl Cl 5-365 Ph CF₃ Br Cl 5-366 Ph CF₃ Cl Br 5-367 Ph Cl CF₃ H 5-368 Ph H CF₃ Cl 5-369 Ph Cl CF₃ Cl 5-370 Ph Br CF₃ Cl 5-371 Ph Cl CF₃ Br 5-372 Ph Cl H CF₃ 5-373 Ph H Cl CF₃ 5-374 Ph Cl Cl CF₃ 5-375 Ph Br Cl CF₃ 5-376 Ph Cl Br CF₃ 5-377 Ph CF₃ Br H 5-378 Ph CF₃ H Br 5-379 Ph CF₃ Br Br 5-380 Ph Br CF₃ H 5-381 Ph H CF₃ Br 5-382 Ph Br CF₃ Br 5-383 Ph Br H CF₃ 5-384 Ph H Br CF₃ 5-385 Ph Br Br CF₃ 5-386 Ph NO₂ H H 5-387 Ph H NO₂ H 5-388 Ph H H NO₂ 5-389 Ph NO₂ Cl H 5-390 Ph NO₂ H Cl 5-391 Ph NO₂ Cl Cl 5-392 Ph NO₂ Br Cl 5-393 Ph NO₂ Cl Br 5-394 Ph Cl NO₂ H 5-395 Ph H NO₂ Cl 5-396 Ph Cl NO₂ Cl 5-397 Ph Br NO₂ Cl 5-398 Ph Cl NO₂ Br 5-399 Ph NO₂ Br H 5-400 Ph NO₂ H Br 5-401 Ph NO₂ Br Br 5-402 Ph Br NO₂ H 5-403 Ph H NO₂ Br 5-404 Ph Br NO₂ Br 5-405 Ph CO₂Me H H 5-406 Ph H CO₂Me H 5-407 Ph H H CO₂Me 5-408 Ph CO₂Me Cl H 5-409 Ph CO₂Me H Cl 5-410 Ph CO₂Me Cl Cl 5-411 Ph CO₂Me Br Cl 5-412 Ph CO₂Me Cl Br 5-413 Ph Cl CO₂Me H 5-414 Ph H CO₂Me Cl 5-415 Ph Cl CO₂Me Cl 5-416 Ph Br CO₂Me Cl 5-417 Ph Cl CO₂Me Br 5-418 Ph Cl H CO₂Me 5-419 Ph H Cl CO₂Me 5-420 Ph Cl Cl CO₂Me 5-421 Ph Br Cl CO₂Me 5-422 Ph Cl Br CO₂Me 5-423 Ph Cl Br Me 5-424 Ph Br Cl Me 5-425 Ph CO₂Me Br H 5-426 Ph CO₂Me H Br 5-427 Ph CO₂Me Br Br 5-428 Ph Br CO₂Me H 5-429 Ph H CO₂Me Br 5-430 Ph Br CO₂Me Br 5-431 Ph Br H CO₂Me 5-432 Ph H Br CO₂Me 5-433 Ph Br Br CO₂Me 5-434 Ph CO₂Et Cl H 5-435 Ph CO₂Et H Cl 5-436 Ph CO₂Et Cl Cl 5-437 Ph CO₂Et Br Cl 5-438 Ph CO₂Et Cl Br 5-439 Ph CO₂Et Br Br 5-440 Ph Cl CO₂Et H 5-441 Ph H CO₂Et Cl 5-442 Ph Cl CO₂Et Cl 5-443 Ph Br CO₂Et Cl 5-444 Ph Cl CO₂Et Br 5-445 Ph Br CO₂Et Br 5-446 Ph H H CO₂Et 5-447 Ph Cl H CO₂Et 5-448 Ph H Cl CO₂Et 5-449 Ph Cl Cl CO₂Et 5-450 Ph Cl Br CO₂Et 5-451 Ph Br Cl CO₂Et 5-452 Ph Br Br CO₂Et 5-453 Ph H H Ac 5-454 Ph Cl H Ac 5-455 Ph H Cl Ac 5-456 Ph Cl Cl Ac 5-457 Ph H H Et 5-458 Ph Cl H Et 5-459 Ph H Cl Et 5-460 Ph Cl Cl Et 5-461 Ph H H Ph 5-462 Ph Cl H Ph 5-463 Ph H Cl Ph 5-464 Ph Cl Cl Ph 5-465 Ph Ph H H 5-466 H Ph Ph H 5-467 H Ph H Ph 5-468 Ph Ph Cl H 5-469 Ph Ph H Cl 5-470 Ph Ph Cl Cl 5-471 Ph Ph Br Cl 5-472 Ph Ph Cl Br 5-473 Ph Ph Br H 5-474 Ph Ph H Br 5-475 Ph Ph Br Br 5-476 Cl Ph Ph H 5-477 Cl Ph Ph Cl 5-478 Br Ph Ph H 5-479 Br Ph Ph Cl 5-480 Br Ph Ph Br 5-481 Cl Ph H Ph 5-482 H Ph Cl Ph 5-483 Br Ph H Ph 5-484 H Ph Br Ph 5-485 Cl Ph Cl Ph 5-486 Br Ph Cl Ph 5-487 Cl Ph Br Ph 5-488 Br Ph Br Ph 5-489 CO₂Et Ph H H 5-490 H Ph CO₂Et H 5-491 H Ph H CO₂Et 5-492 CO₂Et Ph Cl H 5-493 CO₂Et Ph H Cl 5-494 CO₂Et Ph Cl Cl 5-495 Cl Ph CO₂Et H 5-496 H Ph CO₂Et Cl 5-497 Cl Ph CO₂Et Cl 5-498 Cl Ph H CO₂Et 5-499 H Ph Cl CO₂Et 5-500 Cl Ph Cl CO₂Et 5-501 CO₂Et Ph Br H 5-502 CO₂Et Ph H Br 5-503 CO₂Et Ph Cl Br 5-504 CO₂Et Ph Br Cl 5-505 CO₂Et Ph Br Br 5-506 Br Ph CO₂Et H 5-507 H Ph CO₂Et Br 5-508 Br Ph CO₂Et Br 5-509 Cl Ph CO₂Et Br 5-510 Br Ph CO₂Et Cl 5-511 Br Ph H CO₂Et 5-512 H Ph Br CO₂Et 5-513 Br Ph Br CO₂Et 5-514 Cl Ph Br CO₂Et 5-515 Br Ph Cl CO₂Et 5-516 H Ph CO₂Et Me 5-517 Cl Ph CO₂Et Me 5-518 Br Ph CO₂Et Me 5-519 Me Ph CO₂Et H 5-520 Me Ph CO₂Et Cl 5-521 Me Ph CO₂Et Br 5-522 Ph H H NO₂ 5-523 Ph Cl H NO₂ 5-524 Ph H Cl NO₂ 5-525 Ph Cl Cl NO₂

TABLE 6

Compound No. R³ R⁴ R⁷ R⁸ R⁹ R¹⁰ R¹¹ 6-1 H H Me H H H H 6-2 H H H Me H H H 6-3 H H H H Me H H 6-4 H H Cl H H H H 6-5 H H H Cl H H H 6-6 H H H H Cl H H 6-7 H H Br H H H H 6-8 H H H Br H H H 6-9 H H H H Br H H 6-10 H H CF₃ H H H H 6-11 H H H CF₃ H H H 6-12 H H H H CF₃ H H 6-13 H Cl Me H H H H 6-14 H Cl H Me H H H 6-15 H Cl H H Me H H 6-16 H Cl Cl H H H H 6-17 H Cl H Cl H H H 6-18 H Cl H H Cl H H 6-19 H Cl Br H H H H 6-20 H Cl H Br H H H 6-21 H Cl H H Br H H 6-22 H Cl CF₃ H H H H 6-23 H Cl H CF₃ H H H 6-24 H Cl H H CF₃ H H 6-25 H Br Me H H H H 6-26 H Br H Me H H H 6-27 H Br H H Me H H 6-28 H Br Cl H H H H 6-29 H Br H Cl H H H 6-30 H Br H H Cl H H 6-31 H Br Br H H H H 6-32 H Br H Br H H H 6-33 H Br H H Br H H 6-34 H Br CF₃ H H H H 6-35 H Br H CF₃ H H H 6-36 H Br H H CF₃ H H 6-37 H Me Me H H H H 6-38 H Me H Me H H H 6-39 H Me H H Me H H 6-40 H Me Cl H H H H 6-41 H Me H Cl H H H 6-42 H Me H H Cl H H 6-43 H Me Br H H H H 6-44 H Me H Br H H H 6-45 H Me H H Br H H 6-46 H Me CF₃ H H H H 6-47 H Me H CF₃ H H H 6-48 H Me H H CF₃ H H 6-49 Me Cl Me H H H H 6-50 Me Cl H Me H H H 6-51 Me Cl H H Me H H 6-52 Me Cl Cl H H H H 6-53 Me Cl H Cl H H H 6-54 Me Cl H H Cl H H 6-55 Me Cl Br H H H H 6-56 Me Cl H Br H H H 6-57 Me Cl H H Br H H 6-58 Me Cl CF₃ H H H H 6-59 Me Cl H CF₃ H H H 6-60 Me Cl H H CF₃ H H 6-61 Me Br Me H H H H 6-62 Me Br H Me H H H 6-63 Me Br H H Me H H 6-64 Me Br Cl H H H H 6-65 Me Br H Cl H H H 6-66 Me Br H H Cl H H 6-67 Me Br Br H H H H 6-68 Me Br H Br H H H 6-69 Me Br H H Br H H 6-70 Me Br CF₃ H H H H 6-71 Me Br H CF₃ H H H 6-72 Me Br H H CF₃ H H 6-73 Cl Cl Me H H H H 6-74 Cl Cl H Me H H H 6-75 Cl Cl H H Me H H 6-76 Cl Cl Cl H H H H 6-77 Cl Cl H Cl H H H 6-78 Cl Cl H H Cl H H 6-79 Cl Cl Br H H H H 6-80 Cl Cl H Br H H H 6-81 Cl Cl H H Br H H 6-82 Cl Cl CF₃ H H H H 6-83 Cl Cl H CF₃ H H H 6-84 Cl Cl H H CF₃ H H 6-85 Cl Br Me H H H H 6-86 Cl Br H Me H H H 6-87 Cl Br H H Me H H 6-88 Cl Br Cl H H H H 6-89 Cl Br H Cl H H H 6-90 Cl Br H H Cl H H 6-91 Cl Br Br H H H H 6-92 Cl Br H Br H H H 6-93 Cl Br H H Br H H 6-94 Cl Br CF₃ H H H H 6-95 Cl Br H CF₃ H H H 6-96 Cl Br H H CF₃ H H 6-97 Br Br Me H H H H 6-98 Br Br H Me H H H 6-99 Br Br H H Me H H 6-100 Br Br Cl H H H H 6-101 Br Br H Cl H H H 6-102 Br Br H H Cl H H 6-103 Br Br Br H H H H 6-104 Br Br H Br H H H 6-105 Br Br H H Br H H 6-106 Br Br CF₃ H H H H 6-107 Br Br H CF₃ H H H 6-108 Br Br H H CF₃ H H 6-109 Me Me Me H H H H 6-110 Me Me H Me H H H 6-111 Me Me H H Me H H 6-112 Me Me Cl H H H H 6-113 Me Me H Cl H H H 6-114 Me Me H H Cl H H 6-115 Me Me Br H H H H 6-116 Me Me H Br H H H 6-117 Me Me H H Br H H 6-118 Me Me CF₃ H H H H 6-119 Me Me H CF₃ H H H 6-120 Me Me H H CF₃ H H 6-121 H H Me Cl H H H 6-122 H H Me H Cl H H 6-123 H H Me H H Cl H 6-124 H H Me H H H Cl 6-125 H H Cl Me H H H 6-126 H H H Me Cl H H 6-127 H H H Me H Cl H 6-128 H H H Me H H Cl 6-129 H H Cl H Me H H 6-130 H H H Cl Me H H 6-131 H H Cl Cl H H H 6-132 H H Cl H Cl H H 6-133 H H Cl H H Cl H 6-134 H H Cl H H H Cl 6-135 H H H Cl Cl H H 6-136 H H H Cl H Cl H 6-137 H H CF₃ Cl H H H 6-138 H H CF₃ H Cl H H 6-139 H H CF₃ H H Cl H 6-140 H H CF₃ H H H Cl 6-141 H H Cl CF₃ H H H 6-142 H H H CF₃ Cl H H 6-143 H H H CF₃ H Cl H 6-144 H H H CF₃ H H Cl 6-145 H H Cl H CF₃ H H 6-146 H H H Cl CF₃ H H 6-147 H Cl Me Cl H H H 6-148 H Cl Me H Cl H H 6-149 H Cl Me H H Cl H 6-150 H Cl Me H H H Cl 6-151 H Cl Cl Me H H H 6-152 H Cl H Me Cl H H 6-153 H Cl H Me H Cl H 6-154 H Cl H Me H H Cl 6-155 H Cl Cl H Me H H 6-156 H Cl H Cl Me H H 6-157 H Cl Cl Cl H H H 6-158 H Cl Cl H Cl H H 6-159 H Cl Cl H H Cl H 6-160 H Cl Cl H H H Cl 6-161 H Cl H Cl Cl H H 6-162 H Cl H Cl H Cl H 6-163 H Br Me Cl H H H 6-164 H Br Me H Cl H H 6-165 H Br Me H H Cl H 6-166 H Br Me H H H Cl 6-167 H Br Cl Me H H H 6-168 H Br H Me Cl H H 6-169 H Br H Me H Cl H 6-170 H Br H Me H H Cl 6-171 H Br Cl H Me H H 6-172 H Br H Cl Me H H 6-173 H Br Cl Cl H H H 6-174 H Br Cl H Cl H H 6-175 H Br Cl H H Cl H 6-176 H Br Cl H H H Cl 6-177 H Br H Cl Cl H H 6-178 H Br H Cl H Cl H 6-179 H Me Me Cl H H H 6-180 H Me Me H Cl H H 6-181 H Me Me H H Cl H 6-182 H Me Me H H H Cl 6-183 H Me Cl Me H H H 6-184 H Me H Me Cl H H 6-185 H Me H Me H Cl H 6-186 H Me H Me H H Cl 6-187 H Me Cl H Me H H 6-188 H Me H Cl Me H H 6-189 H Me Cl Cl H H H 6-190 H Me Cl H Cl H H 6-191 H Me Cl H H Cl H 6-192 H Me Cl H H H Cl 6-193 H Me H Cl Cl H H 6-194 H Me H Cl H Cl H 6-195 Cl Me Me Cl H H H 6-196 Cl Me Me H Cl H H 6-197 Cl Me Me H H Cl H 6-198 Cl Me Me H H H Cl 6-199 Cl Me Cl Me H H H 6-200 Cl Me H Me Cl H H 6-201 Cl Me H Me H Cl H 6-202 Cl Me H Me H H Cl 6-203 Cl Me Cl H Me H H 6-204 Cl Me H Cl Me H H 6-205 Cl Me Cl Cl H H H 6-206 Cl Me Cl H Cl H H 6-207 Cl Me Cl H H Cl H 6-208 Cl Me Cl H H H Cl 6-209 Cl Me H Cl Cl H H 6-210 Cl Me H Cl H Cl H 6-211 Br Me Me Cl H H H 6-212 Br Me Me H Cl H H 6-213 Br Me Me H H Cl H 6-214 Br Me Me H H H Cl 6-215 Br Me Cl Me H H H 6-216 Br Me H Me Cl H H 6-217 Br Me H Me H Cl H 6-218 Br Me H Me H H Cl 6-219 Br Me Cl H Me H H 6-220 Br Me H Cl Me H H 6-221 Br Me Cl Cl H H H 6-222 Br Me Cl H Cl H H 6-223 Br Me Cl H H Cl H 6-224 Br Me Cl H H H Cl 6-225 Br Me H Cl Cl H H 6-226 Br Me H Cl H Cl H

TABLE 7

Compound No. R³ R⁷ R⁸ R⁹ R¹⁰ 7-1 H H H H H 7-2 Me H H H H 7-3 Et H H H H 7-4 Ph H H H H 7-5 Cl H H H H 7-6 Br H H H H 7-7 CF₃ H H H H 7-8 H Cl H H H 7-9 H H Cl H H 7-10 H H H Cl H 7-11 H H H H Cl 7-12 H Br H H H 7-13 H H Br H H 7-14 H H H Br H 7-15 H H H H Br

TABLE 8

Compound No. R³ R⁴ R⁷ R⁸ R⁹ R¹⁰ R¹¹ 8-1 H H H H H H H 8-2 H Cl H H H H H 8-3 H Br H H H H H 8-4 H NO₂ H H H H H 8-5 H CO₂Me H H H H H 8-6 H CN H H H H H 8-7 H Me H H H H H 8-8 H Et H H H H H 8-9 H Ph H H H H H 8-10 Me H H H H H H 8-11 Me Cl H H H H H 8-12 Me Br H H H H H 8-13 Me NO₂ H H H H H 8-14 Me CO₂Me H H H H H 8-15 Me CN H H H H H 8-16 Me Me H H H H H 8-17 Me Et H H H H H 8-18 Me Ph H H H H H 8-19 Et H H H H H H 8-20 Et Cl H H H H H 8-21 Et Br H H H H H 8-22 Et NO₂ H H H H H 8-23 Et CO₂Me H H H H H 8-24 Et CN H H H H H 8-25 Et Me H H H H H 8-26 Et Et H H H H H 8-27 Et Ph H H H H H 8-28 n-Pr H H H H H H 8-29 n-Pr Cl H H H H H 8-30 n-Pr Br H H H H H 8-31 n-Pr NO₂ H H H H H 8-32 n-Pr CO₂Me H H H H H 8-33 n-Pr CN H H H H H 8-34 n-Pr Me H H H H H 8-35 n-Pr Et H H H H H 8-36 n-Pr Ph H H H H H 8-37 Cl H H H H H H 8-38 Cl Cl H H H H H 8-39 Cl Br H H H H H 8-40 Cl NO₂ H H H H H 8-41 Cl CO₂Me H H H H H 8-42 Cl CN H H H H H 8-43 Cl Me H H H H H 8-44 Cl Et H H H H H 8-45 Cl Ph H H H H H 8-46 Br H H H H H H 8-47 Br Cl H H H H H 8-48 Br Br H H H H H 8-49 Br NO₂ H H H H H 8-50 Br CO₂Me H H H H H 8-51 Br CN H H H H H 8-52 Br Me H H H H H 8-53 Br Et H H H H H 8-54 Br Ph H H H H H 8-55 CF₃ H H H H H H 8-56 CF₃ Cl H H H H H 8-57 CF₃ Br H H H H H 8-58 CF₃ NO₂ H H H H H 8-59 CF₃ CO₂Me H H H H H 8-60 CF₃ CN H H H H H 8-61 CF₃ Me H H H H H 8-62 CF₃ Et H H H H H 8-63 CF₃ Ph H H H H H 8-64 Ph H H H H H H 8-65 Ph Cl H H H H H 8-66 Ph Br H H H H H 8-67 Ph NO₂ H H H H H 8-68 Ph CO₂Me H H H H H 8-69 Ph CN H H H H H 8-70 Ph Me H H H H H 8-71 Ph Et H H H H H 8-72 Ph Ph H H H H H 8-73 Me Cl Me H H H H 8-74 Me Cl H Me H H H 8-75 Me Cl H H Me H H 8-76 Me Cl Cl H H H H 8-77 Me Cl H Cl H H H 8-78 Me Cl H H Cl H H 8-79 Me Cl Br H H H H 8-80 Me Cl H Br H H H 8-81 Me Cl H H Br H H 8-82 Me Cl CF₃ H H H H 8-83 Me Cl H CF₃ H H H 8-84 Me Cl H H CF₃ H H 8-85 Me Br Me H H H H 8-86 Me Br H Me H H H 8-87 Me Br H H Me H H 8-88 Me Br Cl H H H H 8-89 Me Br H Cl H H H 8-90 Me Br H H Cl H H 8-91 Me Br Br H H H H 8-92 Me Br H Br H H H 8-93 Me Br H H Br H H 8-94 Me Br CF₃ H H H H 8-95 Me Br H CF₃ H H H 8-96 Me Br H H CF₃ H H

TABLE 9

Compound No. R³ R⁴ R⁷ R⁸ R⁹ R¹⁰ 9-1 H H H H H H 9-2 H Cl H H H H 9-3 H Br H H H H 9-4 H NO₂ H H H H 9-5 H CN H H H H 9-6 H CF₃ H H H H 9-7 H Me H H H H 9-8 H Et H H H H 9-9 H SMe H H H H 9-10 H CO₂Me H H H H 9-11 Me H H H H H 9-12 Me Cl H H H H 9-13 Me Br H H H H 9-14 Me NO₂ H H H H 9-15 Me CN H H H H 9-16 Me CF₃ H H H H 9-17 Me Me H H H H 9-18 Me Et H H H H 9-19 Me SMe H H H H 9-20 Me CO₂Me H H H H 9-21 Et H H H H H 9-22 Et Cl H H H H 9-23 Et Br H H H H 9-24 Et NO₂ H H H H 9-25 Et CN H H H H 9-26 Et CF₃ H H H H 9-27 Et Me H H H H 9-28 Et Et H H H H 9-29 Et SMe H H H H 9-30 Et CO₂Me H H H H 9-31 Cl H H H H H 9-32 Cl Me H H H H 9-33 Cl Et H H H H 9-34 Cl CN H H H H 9-35 Cl CF₃ H H H H 9-36 Cl Cl H H H H 9-37 Cl Br H H H H 9-38 Cl NO₂ H H H H 9-39 Cl SMe H H H H 9-40 Cl CO₂Me H H H H 9-41 Br H H H H H 9-42 Br Me H H H H 9-43 Br Et H H H H 9-44 Br CN H H H H 9-45 Br CF₃ H H H H 9-46 Br Cl H H H H 9-47 Br Br H H H H 9-48 Br NO₂ H H H H 9-49 Br SMe H H H H 9-50 Br CO₂Me H H H H 9-51 CF₃ H H H H H 9-52 CF₃ Me H H H H 9-53 CF₃ Et H H H H 9-54 CF₃ CN H H H H 9-55 CF₃ CF₃ H H H H 9-56 CF₃ Cl H H H H 9-57 CF₃ Br H H H H 9-58 CF₃ NO₂ H H H H 9-59 CF₃ SMe H H H H 9-60 CF₃ CO₂Me H H H H 9-61 SMe H H H H H 9-62 SMe Cl H H H H 9-63 SMe Br H H H H 9-64 SMe NO₂ H H H H 9-65 SMe CN H H H H 9-66 SMe CF₃ H H H H 9-67 SMe Me H H H H 9-68 SMe Et H H H H 9-69 SMe SMe H H H H 9-70 SMe CO₂Me H H H H 9-71 CN H H H H H 9-72 CN Me H H H H 9-73 CN Et H H H H 9-74 CN CN H H H H 9-75 CN CF₃ H H H H 9-76 CN Cl H H H H 9-77 CN Br H H H H 9-78 CN NO₂ H H H H 9-79 CN SMe H H H H 9-80 CN CO₂Me H H H H 9-81 Me H Me H H H 9-82 Me H H Me H H 9-83 Me H H H Me H 9-84 Me H H H H Me 9-85 Me H F H H H 9-86 Me H H F H H 9-87 Me H H H F H 9-88 Me H H H H F 9-89 Me H Cl H H H 9-90 Me H H Cl H H 9-91 Me H H H Cl H 9-92 Me H H H H Cl 9-93 Me H Br H H H 9-94 Me H H Br H H 9-95 Me H H H Br H 9-96 Me H H H H Br 9-97 Me Cl Me H H H 9-98 Me Cl H Me H H 9-99 Me Cl H H Me H 9-100 Me Cl H H H Me 9-101 Me Cl F H H H 9-102 Me Cl H F H H 9-103 Me Cl H H F H 9-104 Me Cl H H H F 9-105 Me Cl Cl H H H 9-106 Me Cl H Cl H H 9-107 Me Cl H H Cl H 9-108 Me Cl H H H Cl 9-109 Me Cl Br H H H 9-110 Me Cl H Br H H 9-111 Me Cl H H Br H 9-112 Me Cl H H H Br 9-113 Me Br Me H H H 9-114 Me Br H Me H H 9-115 M Br H H Me H 9-116 Me Br H H H Me 9-117 Me Br F H H H 9-118 Me Br H F H H 9-119 Me Br H H F H 9-120 Me Br H H H F 9-121 Me Br Cl H H H 9-122 Me Br H Cl H H 9-123 Me Br H H Cl H 9-124 Me Br H H H Cl 9-125 Me Br Br H H H 9-126 Me Br H Br H H 9-127 Me Br H H Br H 9-128 Me Br H H H Br

TABLE 10

Compound No. R³ R⁷ R⁸ R⁹ R¹⁰ 10-1 H H H H H 10-2 Me H H H H 10-3 Et H H H H 10-4 n-Pr H H H H 10-5 Cl H H H H 10-6 Br H H H H 10-7 Sme H H H H 10-8 CF₃ H H H H 10-9 CN H H H H 10-10 H Me H H H 10-11 H H Me H H 10-12 H H H Me H 10-13 H H H H Me 10-14 H F H H H 10-15 H H F H H 10-16 H H H F H 10-17 H H H H F 10-18 H Cl H H H 10-19 H H Cl H H 10-20 H H H Cl H 10-21 H H H H Cl 10-22 H Br H H H 10-23 H H Br H H 10-24 H H H Br H 10-25 H H H H Br 10-26 Me Me H H H 10-27 Me H Me H H 10-28 Me H H Me H 10-29 Me H H H Me 10-30 Me F H H H 10-31 Me H F H H 10-32 Me H H F H 10-33 Me H H H F 10-34 Me Cl H H H 10-35 Me H Cl H H 10-36 Me H H Cl H 10-37 Me H H H Cl 10-38 Me Br H H H 10-39 Me H Br H H 10-40 Me H H Br H 10-41 Me H H H Br 10-42 Et Me H H H 10-43 Et H Me H H 10-44 Et H H Me H 10-45 Et H H H Me 10-46 Et F H H H 10-47 Et H F H H 10-48 Et H H F H 10-49 Et H H H F 10-50 Et Cl H H H 10-51 Et H Cl H H 10-52 Et H H Cl H 10-53 Et H H H Cl 10-54 Et Br H H H 10-55 Et H Br H H 10-56 Et H H Br H 10-57 Et H H H Br 10-58 Cl Me H H H 10-59 Cl H Me H H 10-60 Cl H H Me H 10-61 Cl H H H Me 10-62 Cl F H H H 10-63 Cl H F H H 10-64 Cl H H F H 10-65 Cl H H H F 10-66 Cl Cl H H H 10-67 Cl H Cl H H 10-68 Cl H H Cl H 10-69 Cl H H H Cl 10-70 Cl Br H H H 10-71 Cl H Br H H 10-72 Cl H H Br H 10-73 Cl H H H Br 10-74 Br Me H H H 10-75 Br H Me H H 10-76 Br H H Me H 10-77 Br H H H Me 10-78 Br F H H H 10-79 Br H F H H 10-80 Br H H F H 10-81 Br H H H F 10-82 Br Cl H H H 10-83 Br H Cl H H 10-84 Br H H Cl H 10-85 Br H H H Cl 10-86 Br Br H H H 10-87 Br H Br H H 10-88 Br H H Br H 10-89 Br H H H Br

TABLE 11

Compound No. R⁷ R⁸ R⁹ R¹⁰ R¹¹ 11-1 H H H H H 11-2 Me H H H H 11-3 H Me H H H 11-4 H H Me H H 11-5 Et H H H H 11-6 H Et H H H 11-7 H H Et H H 11-8 F H H H H 11-9 H F H H H 11-10 H H F H H 11-11 Cl H H H H 11-12 H Cl H H H 11-13 H H Cl H H 11-14 Br H H H H 11-15 H Br H H H 11-16 H H Br H H 11-17 CF₃ H H H H 11-18 H CF₃ H H H 11-19 H H CF₃ H H 11-20 OCF₃ H H H H 11-21 H OCF₃ H H H 11-22 H H OCF₃ H H 11-23 Ph H H H H 11-24 H Ph H H H 11-25 H H Ph H H 11-26 Oph H H H H 11-27 H OPh H H H 11-28 H H OPh H H 11-29 Bn H H H H 11-30 H Bn H H H 11-31 H H Bn H H 11-32 CO₂Me H H H H 11-33 H CO₂M H H H 11-34 H H CO₂Me H H 11-35 CN H H H H 11-36 H CN H H H 11-37 H H CN H H 11-38 NO₂ H H H H 11-39 H NO₂ H H H 11-40 H H NO₂ H H 11-41 Ome H H H H 11-42 H OMe H H H 11-43 H H OMe H H 11-44 Me Cl H H H 11-45 Me H Cl H H 11-46 Me H H Cl H 11-47 Me H H H Cl 11-48 Cl Me H H H 11-49 H Me Cl H H 11-50 H Me H Cl H 11-51 H Me H H Cl 11-52 Cl H Me H H 11-53 H Cl Me H H 11-54 Me Me H H H 11-55 Me H Me H H 11-56 Me H H Me H 11-57 Me H H H Me 11-58 H Me Me H H 11-59 H Me H Me H 11-60 Cl Cl H H H 11-61 Cl H Cl H H 11-62 Cl H H Cl H 11-63 Cl H H H Cl 11-64 H Cl Cl H H 11-65 H Cl H Cl H

Next, methods for preparing the compound of the invention will be explained below. However, the present invention should not be construed as being limited thereto.

(Preparation Method 1)

The compound of the invention can be prepared by reacting a compound of the formula (2) A-H  (2) wherein A has the same meaning as defined above, with a compound of the formula (3)

wherein R¹, R² and Y have the same meanings as defined above, and X is halogen. (Preparation Method 2)

The compound of the invention can be prepared by reacting a compound of the formula (4)

wherein B and Y have the same meanings as defined above, with a compound of the formula (5) R¹R²NSO₂X wherein R¹ and R² have the same meanings as defined above and X is halogen. (Preparation Method 3)

The compound of the invention can be prepared by oxidizing a compound of the formula (6)

wherein R¹, R², A and Y have the same meanings as defined above, with an oxidizing agent.

In (Preparation Method 1), a sulfamoyl derivative (1) can be synthesized by reacting (2) with a halosulfonyltriazole (3) in the presence of a base.

The solvent may be any solvent so far as it is inert to the reaction. There may be employed, for example, ethers such as dioxane, dimethoxyethane and tetrahydrofuran, aromatic hydrocarbons such as toluene, xylene and chlorobenzene, halogenated hydrocarbons such as dichloroethane and chloroform, ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone, nitriles such as acetonitrile, tertiary amines such as pyridine, triethylamine and tributylamine, amides such as N,N-dimethylformamide, sulfur compounds such as dimethyl sulfoxide and sulfolane, nitro compounds such as nitrorethane and nitrobenzene, esters such as methyl acetate, or mixtures thereof. The reaction can be performed at a reaction temperature from −78° C. to the boiling point of the solvent.

As for the base, there may be employed, for example, organic bases such as pyridine, 4-dimethylaminopyridine, triethylamine, diethylisopropylamine and N,N-diethylaniline, inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate and potassium hydrogen carbonate, metal hydrides such as sodium hydride, metal alkoxides such as sodium methoxide and potassium t-butoxide, organic metal amides such as lithium diisopropylamide, organic metal compounds such as n-butyl lithium, and the like.

In the (Preparation Method 2), the sulfamoyl derivative (1) can be synthesized by reacting (4) with a dialkylsulfamoyl halide (5) in the presence of a base.

The solvent may be any solvent so far as it is inert to the reaction. There may be employed, for example, ethers such as dioxane, dimethoxyethane and tetrahydrofuran, aromatic hydrocarbons such as toluene, xylene and chlorobenzene, halogenated hydrocarbons such as dichloroethane and chloroform, ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone, nitriles such as acetonitrile, tertiary amines such as pyridine, triethylamine and tributylamine, amides such as N,N-dimethylformamide, sulfur compounds such as dimethyl sulfoxide and sulfolane, nitro compounds such as nitroethane and nitrobenzene, esters such as methyl acetate, or mixtures thereof. The reaction can be p rformed at a reaction temperature from −78° C. to the boiling point of the solvent.

As for the base, there may be employed, for example, organic bases such as pyridine, 4-dimethylaminopyridine, triethylamine, diethylisopropylamine and N,N-diethylaniline, inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate and potassium hydrogen carbonate, metal hydrides such as sodium hydride, metal alkoxides such as sodium methoxide and potassium t-butoxide, organic metal amides such as lithium diisopropylamide, organic metal compounds such as n-butyl lithium, and the like.

In the (Preparation Method 3), the sulfamoyl derivative (1) can be synthesized by oxidizing (6) with an oxidizing agent.

The solvent may be any solvent so far as it is inert to the reaction. There may be employed, for example, ethers such as dioxane, dimethoxyethane and tetrahydrofuran, aromatic hydrocarbons such as toluene, xylene and chlorobenzene, halogenated hydrocarbons such as dichloroethane and chloroform, ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone, nitriles such as acetonitrile, amides such as N,N-dimethylformamide, esters such as ethyl acetate, carboxylic acids such as acetic acid, water, or mixtures thereof. The reaction can be performed at a reaction temperature from −78° C. to the boiling point of the solvent.

As for the oxidizing agent, there may be employed, for example, peroxides such as hydrogen peroxide, peracetic acid, 3-chloro perbenzoic acid, sodium percarbonate, and the like.

The starting compounds of the method, compounds (2), (3), (4) and (6) can be readily synthesized by known methods (see Dai Yuki Kagaku vol. 14, 299–514 for the compound (2), JP-A-5-43557 and/or JP-A-7-215971 for the compound (3), Chem. Pharm. Bull. 41(7) 1226–1231 (1993) for the compound (4), and JP-A-9-143181 for the compound (6).) or methods analogous thereto.

As for the plant diseases which are target for control by the compound of the invention, there may be mentioned: rice blast (Pyricularia oryzae), helminthosporium leaf spot (Cochliobolus miyabeanus), sheath blight (Rhizoctonia solani), barley and wheat: powdery mildew (Erysiphe graminis f. sp. hordei, f. sp. tritici), stripe (Pyrenophora graminea), net blotch (Pyrenophora teres), scab (Gibberella zeae), rust (Puccinia struiformis, P. graminis, P. recondita, P. hordei), snow blight (Tipula sp., Micronectriella nivais), loose smut (Ustilago tritici, U. nuda), eye spot (Pseudocercosporella herpotrichoides), scald (Rhynchosporium secalis), spekled leaf blotch (Septoria tritici), glume blotch (Leptosphaeria nodorum), citrus: melanose (Diaporthe citri), scab (Elsinoe fawcetti), green mold and blue mold (Penicillium digitalum, P. italicum), apple: blossom blight (Sclerotinia mali), canker (Valsa mali), powdery mildew (Podosphaera lcucotricha), alternaria leaf spot (Alternaria mali), scab (Venturia inaequalis), pear: scab (Venturia nashicola), black spot (Alternaria kikuchiana), rust (Gymnosporangium haracanum), peach: brown rot (Sclerolinia cinerea), scab (Clcadosporium carpophilum), phomopsis rot (Phomopsis sp.), grape: downy mildew (Plasmopara viticola), anthracnose (Elsinoe ampelina), ripe rot (Glomerella cingulata), powdery mildew (Uncinula necator), rust (Phakopsora ampelopsidis), kaki: anthracnose (Gloeosporium kakj), angular leaf spot and circular leaf spot (Cercospora kakj, Mycosphaerella nawae), melons: downy mildew (Pseudoperenospora cubensis), anthracnose (Colletotrichum lagenarium), powdery mildew (Sphaerotheca fuliginea), gummy stem blight (Mycosphaerella melonis), tomato: late blight (Phytophthora infestans), early blight (Alternaria solani), leaf mold (Cladosporium fulvum), egg plant: brown spot (Phomopsis vexans), powdery mildew (Erysiphe cichoracoarum), rape: black rot (Alternaria japonica), white rot (Cercosporella brassicae), oion: rust (Puccinia allii), soybean: purple stain of seed (Cercospora kikuchii), sphaceloma scab (Elisinoe glycines), black spot (Diaporthe phaseololum), kidney bean: anthracnose (Colletotrichum lindemuthianum), peanut: leaf spot (Mycosphaerella personatum), brown leaf spot (Cercospora arachidicola), pea: powdery mildew (Erysiphe pisi), potato: late blight (Alternaria solani), strawberry: powdery mildew (Sphaerotheca humuli), tea plant: net blister blast (Exobasidium reticulatum), white scab (Elsinoe leucospila), tobacco: brown spot (Alternaria lingipes), powdery mildew (Erysiphe cichoracearum), anthracnose (Colletotrichum tabacum), beet: cercospora leaf (Cercospora beticola), rose: black spot (Diplocarpon rosae), powdery mildew (Sphaerotheca pannosa), chrysanthemum: leaf spot (Septoria chrysanthemuindici), rust (Puccinia horiana), various crops: gray mold (Botrytis cinerea), various crops: sclerotinia rot (Sclerotinia sclerotiorum), and the like.

Upon use of the compound of the invention as agricultural and horticultural fungicides, they are generally mixed with a suitable carrier, for example, solid carriers such as clay, talc, bentonite and diatomaceous earth, or liquid carriers such as water, alcohols (methanol, ethanol, etc.), aromatic hydrocarbons (benzene, toluene, methylnaphthalene, etc.), chlorinated hydrocarbons, ethers, ketones, esters (ethyl acetate, etc.), acid amides (dimethylformamide, etc.), or the like to be applied. If desired, emulsifying agents, dispersants, suspension agents, penetrating agents, spreading agents, stabilizers and the like may be added so that the compounds can be subjected to practical application in any of formulation forms such as liquid formulation, emulsifiable concentrate, wettable powder, dust formulation, granule, or flowable powder.

The compound of the invention can be mixed or used in combination with various active compounds such as fungicides, bactericides, acaricides, nematicides and insecticides or other biologically active compounds. Common names of these active compounds will be listed below concretely. However, the invention should not be construed as being limited thereto.

Fungicidally active compounds: acibenzolar, ampropyfos, anilazine, azaconazole, azoxystrobin, benalaxyl, benodail, benomyl, benzamacril, binapacryl, biphenyl, bitertanol, bethoxazine, bordeaux mixture, blasticidin-S, bromoconazole, bupirimate, buthiobate, calcium polysulfide, captafol, captan, copper oxychloride, carpropamid, carbendazim, carboxin, chinom thionat, chlobenthiazone, chlorfenazol, chloroneb, chlorothalonil, chlozolinate, cufraneb, cymoxanil, cyproconazol, cyprodinil, cyprofuram, debacarb, dichlorophen, dichlobutrazol, dichlofluanid, dichlormedine, dichloran, diethofencarb, dichlocymet, difenoconazole, diflumetorim, dimethirimol, dimethomorph, diniconazole, diniconazole-M, dinocap, diphenylamine, dipyrithione, ditalimfos, dithianon, dodemorph, dodine, drazoxolon, edifenphos, epoxiconazole, etaconazole, ethirimol, etridiazole, famoxadone, fenarimol, febuconazole, fenfuram, fenpiclonil, fenpropidin, fenpropimorph, fentin, ferbam, ferimzone, fluazinam, fludioxonil, fluoroimide, fluquinconazole, flusilazole, flusulfamide, flutolanll, flutriafol, folpet, fosetyl-aluminium, fuberidazole, furalaxyl, fenamidone, fenhexamid, guazatine, hexachlorobenzene, hexaconazole, hymexazol, imazalil, imibenconazol, iminoctadine, ipconazole, iprobenfos, iprodione, isoprothiolane, iprovalicarb, kasugamycin, kresoxim-methyl, mancopper, mancozeb, maneb, mepanipyrim, mepronil, metalaxyl, metconazole, metiram, metominostrobin, myclobutanil, nabam, nickel bis(dimethyldithiocarbamate), nitrothal-isopropyl, nuarimol, octhilinone, ofurace, oxadixyl, oxycarboxin, oxpoconazole fumarate, pefurzoate, penconazole, pencycuron, phthalide, piperalin, polyoxins, probenazole, prochloraz, procymidone, propamocarb hydrochloride, propiconazole, propineb, pyrazophos, pyrifenox, pyrimethanil, pyroquilon, quinoxyfen, quintozene, sulfur, spiroxamine, tebuconazole, tecnazene, tetraconazole, thiabendazole, thifluzamide, thiophanate-methyl, thiram, tolclofos-methyl, tolylfluanid, triadimefon, toriadimenol, triazoxide, tricyclazole, tridemorph, triflumizole, triforine, triticonazole, validamycin, vinclozolin, zineb, ziram.

Bactericidally active compounds: streptomycin, oxyterracycline, oxolinic acid.

Nematicidally active compounds: aldoxycarb, fosthiazate, fosthietan, oxamyl, fenamiphos.

Acaricidally active compounds: amitraz, bromopropylate, chinomethionat, chlorobenzilate, clofentezine, cyhexatine, dicofol, dienochlor, ethoxazole, fenazaquin, fenbutatin oxide, fenpropathrin, fenproximate, halfenprox, hexythiazox, milbemectin, propargite, pyridaben, pyrimidifen, tebufenpyrad,

Insecticidally active compounds: abamectin, acephate, acetamipirid, azinphos-methyl, bendiocarb, benfuracarb, bensultap, bifenthrin, buprofezin, butocarboxim, carbaryl, carbofuran, carbosulfan, cartap, chlorfenapyr, chlorpyrifos, chlorfenvinphos, chlorfluazuron, clothianidin, chlromafenozide, chlorpyrifos-methyl, cyfluthrin, beta-cyfluthrin, cypermethrin, cyromazine, cyhalothrin, lambda-cyhalothrin, deltamethrin, diafenthiuron, diazinon, diacloden, diflubenzuron, dimethylvinphos, diofenolan, disulfoton, dimethoate, EPN, esfenvalerate, ethiofencarb, ethiprole, etofenprox, etrimfos, fenitrothion, fenobucarb, fenoxycarb, fenpropathrin, fenvalerate, fipronil, flucythrinate, flufenoxuron, flufenprox, tau-fluvalinate, fonophos, formetanate, formothion, furathiocarb, halofenozide, hexaflumuron, hydramethylnon, imidacloprid, isofenphos, indoxacarb, isoprocarb, isoxathion, lufenuron, malathion, metaldehyde, metahamidophos, methidathion, methacrifos, metalcarb, methomyl, methoprene, methoxychlor, methoxyfenozide, monocrotophos, muscalure, nitenpyram, omethoate, oxydemeton-methyl, oxamyl, parathion, parathion-methyl, permethrin, phenthoate, phoxim, phorate, phosalone, phosmet, phosphamidon, pirimicarb, pirimiphos-methyl, profenofos, pymetrozine, pyraclofos, pyriproxyfen, rotenone, sulprofos, silafluofen, spinosad, sulfotep, tebfenozide, teflubenzuron, tefluthorin, terbufos, tetrachlorovinphos, thiodicarb, thiamethoxam, thiofanox, thiometon, tolfenpyrad, tralomethrin, trichlorfon, triazuron, triflumuron, vamidothion.

When used as agricultural and horticultural fungicides, the compounds of the invention can be applied by foliage application, soil treatment, seed disinfection and the like. They are also effective in general methods usually utilized by those skilled in the art.

Further, if necessary, other herbicides, and various insecticides, fungicides, plant growth regulators, synergists and the like may be mixed at formulation or spraying and used together. An application rate of the compound of the invention varies due to an application field, an application period, an application method, a target disease, a cultured crop and the like, but generally it is suitable to apply about 0.005–50 kg of the active ingredient per hectare.

Next, formulation examples of fungicides containing the compound of the invention as active ingredients are shown as follows. However, the present invention should not be construed as being limited thereto. In the following formulatlon examples, all “parts” means are “parts by weight”.

Formulation Example 1 Emulsifiable Concentrate Compound of the invention 20 parts Methylnaphthalene 55 parts Cyclohexanone 20 parts Sorpol 2680 (mixture of nonionic surfactant 5 parts and anionic surfactant: Toho Kagaku Kogyo K.K., trade name)

The above components are mixed uniformly to make an emulsion. Upon use, the emulsion is diluted by 50–20,000 times to apply 0.005–50 kg of the active ingredient per hectare.

Formulation Example 2 Wettable Powder Compound of the invention 25 parts Zeeklite PEP (mixture of kaolinite and celisite: 66 parts Zeeklite Industry K.K., Ltd.) Solpol 5039 (anionic surfactant: Toho Kagaku Kogyo 4 parts K.K., trade name) Carplex #80 (white carbon: Shionogi Seiyaku K.K., 3 parts trade name) Calcium ligninsulfonate 2 parts

The above components are mixed and grounded uniformly to make a wattable powder. Upon use, the wettable powder is diluted to 50 to 20,000 times to spray 0.005 to 50 kg of active ingredient per hectare.

Formulation Example 3 Dust Formulation Compound of the invention 3 parts Carplex #80 (white carbon: Shionogi Seiyaku K.K., 0.5 part trade name) Clay 95 parts Diisopropyl phosphate 1.5 parts

The above components are mixed and grounded uniformly to make a dust formulation. Upon use, the dust formulation is applied with 0.005 to 50 kg of active ingredient per hectare.

Formulation Example 4 Granule Compound of the invention 5 parts Bentonite 30 parts Talc 64 parts Calcium ligninsulfonate 1 part

The above components are mixed and grounded uniformly, stirred to mix with addition of a small amount of water, granulated by an extrusion granulator and dried to make a granule. Upon use, the granule is applied with 0.005 to 50 kg of active ingredient per hectare.

Formulation Example 5 Flowable Powder Compound of the invention 25 parts Solpol 3353 (nonionic surfactant: Toho Kagaku Kogyo 5 parts K.K., trade name) Lunox 1000C (anionic surfactant: Toho Kagaku Kogyo 0.5 part K.K., trade name) Xanthan gum (natural polymer) 0.2 part Sodium benzoate 0.4 part Propylene glycol 10 parts Water 58.9 parts

The above components except for the active ingredient (the compound of the invention) are dissolved uniformly, to which the compound of the invention is added, stirred well, and thereafter water-grounded in a sand mill to obtain a flowable powder. Upon use, the flowable powder is diluted by 50–20,000 times to apply 0.005–50 kg of the active ingredient per hectare.

BEST MODE FOR CARRYING OUT THE INVENTION

Next, the present invention will be explained concretely by examples. However, the present invention should not be construed as being limited thereto.

EXAMPLE 1 Preparation of 1-(N,N-dimethylsulfamoyl)-3-(2-methyl-3-chloroindol-1-yl)sulfonyl-1,2,4-triazole (1-33(a))

0.6 g of 2-methyl-3-chloroindole was dissolved in 20 ml of tetrahydrofuran, and 0.17 g of sodium hydride (55% or more) was added thereto with stirring under ice-cooling. After stirring at room temperature for 1 hour, the solution was ice-cooled again and 1.0 g of 1-N,N-dimethylsulfamoyl-3-chlorosulfonyl-1,2,4-triazole was added, and then the mixture was stirred at room temperature for 3 hours. After completion of the reaction, diluted hydrochloric acid was added and the reaction mixture was extracted with ethyl acetate. After distilling off the solvent, the residue was purified by column chromatography to obtain 0.73 g of the titled compound.

EXAMPLE 2 Preparation of 1-(N,N-dimethylsulfamoyl)-3-(3-chloroindazol-1-yl)sulfonyl-1,2,4-triazole (7-5(a))

0.5 g of 3-chloroindazole was dissolved in 20 ml of tetrahydrofuran, and 0.4 g of triethylamine was added thereto with stirring under ice-cooling. Thereafter, 0.94 g of 1-N,N-dimethylsulfamoyl-3-chlorosulfonyl-1,2,4-triazole was added, and then the mixture was stirred at room temperature for 16 hours. After completion of the reaction, the reaction mixture was neutralized with diluted hydrochloric acid, and extracted with ethyl acetate. After distilling off the solvent, the residue was purified by column chromatography to obtain 0.94 g of the titled compound.

EXAMPLE 3 Preparation of 1-(N,N-dimethylsulfamoyl)-3-(3-phenyl-4-chloro-5-methylpyrazol-1-yl)sulfonyl-1,2,4-triazole (8-11(a))

0.56 g of 3-phenyl-4-chloro-5-methylpyrazole was dissolved in 20 ml of tetrahydrofuran, and 0.47 g of triethylamine was added thereto with stirring under ice-cooling. Thereafter, 0.8 g of 1-N,N-dimethylsulfamoyl-3-chlorosulfonyl-1,2,4-triazole was added, and then the mixture was stirred at room temperature for 16 hours. After completion of the reaction, the reaction mixture was neutralized with diluted hydrochloric acid, and extracted with ethyl acetate. After distilling off the solvent, the residue was purified by column chromatography to obtain 1.04 g of the titled compound.

EXAMPLE 4 Preparation of 1-dimethylsulfamoyl-3-(4-trifluoromethylbenzoyl)-1,2,4-triazole (11-19(a))

0.31 g of 3- (4-trifluoromethylbenzoyl)-1,2,4-triazole was dissolved in 3 ml of DMF, 0.21 g of potassium carbonate was added thereto, and then 0.22 g of dimethylsulfamoyl chloride was added at room temperature with stirring. After stirring the reaction mixture for 1.5 hours at room temperature, water was added to precipitate crystals, and the crystals were collected by filtration and washed with diethyl ether. Drying of the mixture under reducing pressure afforded 0.31 g of the titled compound.

EXAMPLE 5 Preparation of 1-dimethylsulfamoyl-3-(2-methylimidazo[1.2-a]pyridin-3-ylsulfonyl)-1,2,4-triazole (10-2(a))

1.2 g of 1-dimethylsulfamoyl-3-(2-methylimidazo[1.2-a]pyridin-3-ylsulfenyl)-1,2,4-triazole was dissolved in a mixture of 20 ml of acetonitrile and 20 ml of water, and 3.0 g of sodium percarbonate was added thereto at room temperature. After stirring the mixture for 1 hour at room temperature, additional 3.0 g of sodium percarbonate was added. After completion of the reaction, the reaction mixture was neutralized with diluted hydrochloric acid and extracted with ethyl acetate. Aft r distilling off the solvent, the residue was purified by column chromatography to obtain 0.3 g of the titled compound.

Next, the physical properties of the compounds of the formula (1) prepared according to these methods are shown in Table 12.

TABLE 12 Compound No. Property (m.p. ° C.)  1-1(a)  98–100  1-2(a) 74–76  1-3(a) 70–72  1-4(a) 70–72  1-9(a) 136–139  1-10(a) 118–121  1-11(a) 138–139  1-12(a) 138–139  1-13(a) 96–98  1-14(a) Oil  1-20(a) 125–126  1-21(a) 120–122  1-22(a) 118–121  1-23(a) 78–79  1-26(a)   141–142.5  1-27(a) 60–61  1-31(a) 158–161  1-32(a) 145.5–146.5  1-33(a) 120–122  1-34(a) 81–82  1-35(a) 71–72  1-38(a) 128–129  1-41(a) 151–154  1-42(a) 140–141  1-42(i) Oil  1-42(k) 142–145  1-42(l) 167.5–171    1-43(a) 118.5–120    1-44(a) 149–150  1-45(a) Oil  1-50(a) 124–126  1-51(a) 181–182  1-56(a) 94–95  1-57(a) 61–63  1-62(a) 147.5–149    1-63(a) 134.5–136    1-71(a)   159–159.5  1-72(a) 104–107  1-81(a) 163–165  1-105(a) 135–137  1-118(a) 137–140  1-119(a) 139–140  1-125(a) 129–131  1-126(a) 119–121  1-130(a) 142–145  1-131(a) 128–129  1-133(a) 113–115  1-135(a) 80–81  1-136(c) 134.5–135.5  1-148(a) 112–113  1-152(a) 120–122  1-161(a) Oil  1-163(a) 134.5–136    1-168(a)   138–139.5  1-187(a) 172–174  1-188(a) 166–168  1-211(a) 94–95  1-222(a) 126–127  1-232(a) 172–174  1-233(a) 164–165  1-243(a) Oil  1-258(a) 125–128  1-265(a)   142–143.5  1-266(a) 114–117  1-276(a) 177.5–179    1-276(j) 87–89  1-277(a) 132–133  1-283(a) 112–113  1-289(a) 138.5–139.5  1-290(a) 142–143  1-298(a) 90–92  1-311(a) 142–143  1-316(a)   65–66.5  1-316(j) 91–92  1-326(a) 82–84  1-343(a) Oil  1-353(a) 160–163  1-370(a) Oil  1-378(a) 93–94  1-396(a) 149–151  1-403(a) 129–131  1-414(a) 151.5–153    1-421(a)   107–108.5  1-435(a) 184–186  1-440(a) 194.5–195.5  1-445(a) 50–53  1-470(a) 120–122  1-497(a) 119–121  1-508(a) 148–150  1-518(a) Oil  1-537(a) 153–155  1-548(a) 204–206 (decomposition)  1-557(a) Oil  1-568(a) 51–53  2-2(a) 134–135  2-2(b) 160–161  2-2(n) 184–186  2-2(o)   180–181.5  2-3(b) 140.5–142    2-3(n) 151.5–152.5  2-3(o) 162.5–163    2-4(b) 176–180  2-5(a) 143–144  2-5(b) 174–176  2-6(a) 104–105  2-6(d) 141–143  2-6(e) 168–169  2-6(n) 173–175  2-7(a) 117–118  2-7(b) 142–145  2-7(n) 143–144  2-8(b) 177–179  2-8(x) 123–124  2-10(a) 112.5–114    2-10(b) 143–145  2-10(n)   163–164.5  2-10(v) 138–141  2-11(e)   149–150.5  2-14(a) 85.5–87    2-14(b) 150.5–153    2-17(a) 145–147  2-17(b) 181–183  2-18(a) 86–87  2-18(b) 134–136  2-19(a) 82–83  2-19(b) 136–138  2-20(a) 109–110  2-20(b) 148–149  2-24(a) 61–63  2-24(b) 81–83  2-26(a) 126.5–127.5  2-30(a) 177–179  2-30(b) 174–176  2-34(a) 156–157  2-34(b) 181–183  2-39(e) 126–128  2-44(b) 162–163  3-1(a) 160–162  5-1(a) 115–118  5-22(a) Oil  5-23(a) 39–42  5-34(a) 55–58 (decomposition)  5-58(a) 44–47  5-82(a) 121–123  5-146(a) 182–184  5-146(h) 145.5–147.5  5-153(a) 139–140  5-165(a)   128–129.5  5-227(a) 42–45  5-234(a) Oil  5-247(a) Oil  5-254(a) 68–70  5-254(h) Oil  5-261(a) 151–154  5-274(a) 173–176  5-490(a) 126–129  5-495(a)   149–150.5  5-506(a) 145–147  6-6(a) 163.5–164.5  6-30(a) 54–56  7-1(a), (b) 135–137 (mixture)  7-2(e) 135–136  7-5(a) 164–165  8-1(a) 154.5–155.5  8-10(a) 110.5–111    8-11(a) 125–128 10-2(a) 179.5–181   11-1(a) 81–82 11-17(a) 89–91 11-18(a) 62–63 11-19(a) 121–122 11-24(a) 133–135

Usefulness of the compound of the invention will be explained concretely by the following test examples. However. the present invention should not be construed as being limited thereto.

TEST EXAMPLE 1 Test on Cucumber Downy Mildew Controlling Effect

Cucumber (species: Sagami Hanjiro) grown in a pot having a diameter of 7 cm was applied at 1.5 leaf stage by means of a spray-gun with 20 ml per a pot of agent solution which was prepared by diluting the emulsifiable concentrate of the compound of the invention with water to 500 ppm.

A day after application, spore suspension of cucumber downy midlew pathogen (Pseudoperonospora cubensis) (2×10⁵ /ml) was sprayed for inoculation. Inoculated cucumber was placed in an inoculation box at a temperature of 25° C. and a humidity of 95% or more for one day and night. Thereafter, the cucumber was placed in a greenhouse and determined a ratio of disease spot area formed after 7 days from inoculation to inoculated leaves to calculate a control value according to the following equation: control value=[1-(disease spot area proportion in treated part/disease spot area proportion in non-treated part)]×100

As a result, the following compounds showed a controlling value of 100.

The compound of the invention No.: 1-1(a), 1-2(a), 1-3(a), 1-4(a), 1-9 (a), 1-10(a), 1-11(a), 1-12(a), 1-13(a), 1-14(a), 1-20(a), 1-21(a), 1-22(a), 1-23(a), 1-32(a), 1-33(a), 1-34(a), 1-35(a), 1-38(a), 1-41(a), 1-42(a), 1-43(a), 1-44(a), 1-45(a), 1-50(a), 1-51(a), 1-56(a), 1-62(a), 1-63(a), 1-71(a), 1-72(a), 1-81(a), 1-105(a), 1-118(a), 1-119(a), 1-125(a), 1-126(a), 1-130(a), 1-131(a), 1-133(a), 1-135(a), 1-136(c), 1-148(a), 1-152(a), 1-161(a), 1-163(a), 1-168(a), 1-187(a), 1-188(a), 1-211(a), 1-222(a), 1-232(a), 1-233(a), 1-243(a), 1-258(a), 1-265(a), 1-266(a), 1-276(a), 1-277(a), 1-283(a), 1-289(a), 1-290(a), 1-298(a), 1-311(a), 1-316(a), 1-326(a), 1-343(a), 1-353(a), 1-370(a), 1-378(a), 1-396(a), 1-403(a), 1-414(a), 1-421(a), 1-435(a), 1-440(a), 1-445(a), 1-470(a), 1-497(a), 1-508(a), 1-518(a), 1-537(a), 1-548(a), 1-568(a), 2-2(a), 2-2(b), 2-2(n), 2-2(o), 2-3(b), 2-3(n), 2-3(o), 2-4(b), 2-5(a), 2-5(b), 2-6(a), 2-6(d), 2-6(e), 2-6(n), 2-7(a), 2-7(b), 2-7(n), 2-8(b), 2-8(x), 2-10(a), 2-10(b), 2-10(n), 2-10(v), 2-11(e), 2-14(a), 2-14(b), 2-17(a), 2-17(b), 2-18(a), 2-18(b), 2-19(a), 2-19(b), 2-20(a), 2-20(b), 2-24(a), 2-24(b), 2-26(a), 2-34(a), 2-34(b), 2-39(e), 2-44(b), 3-1(a), 5-1(a), 5-22(a), 5-23(a), 5-34(a), 5-58(a), 5-82(a), 5-146(a), 5-153(a). 5-165(a), 5-227(a), 5-234(a), 5-247(a), 5-254(a), 5-261(a), 5-274(a), 5-490(a), 5-495(a), 5-506(a), 6-6(a), 6-30(a), 7-1(a), (b), 7-2(e), 7-5(a), 8-1(a), 8-10(a), 8-11(a), 10-2(a), 11-1(a), 11-17(a), 11-18(a), 11-19(a). 11-24(a).

INDUSTRIAL APPLICABILITY

These compounds are novel, exhibit excellent agricultural and horticultural fungicidal effect and have no phytotoxicity on useful crops so that they are useful as agricultural and horticultural fungicides. 

1. A process for producing a sulfamoyl compound of the formulae (1):

wherein R¹ and R² are each independently C₁₋₄ alkyl, or R¹ and R² together are C₄₋₆ alkylene or C₄₋₆ alkyleneoxy, Y is H, halogen, C₁₋₈ alkyl, C₁₋₄ alkoxy, C₁₋₈ alkylthio, C₁₋₈ haloalkyl, C₁₋₈ haloalkoxy or C₁₋₈ haloalkylthio, A is

B is A-1 to A-10, or

W is a chemical bond or O, V is O or S, D, E, F and G are each independently N, CR⁷, CR⁸, C⁹ or CR¹⁰, and R³, R⁴, R₅, R^(6, R) ⁷, R⁸, R⁹, R¹⁰ and R¹¹ are each independently H, C₁₋₈ alkyl, C₃₋₈ cycloalkyl, C₂₋₈ alkenyl, C₅₋₈ cycloalkenyt, C₂₋₈ alkynyl, C₁₋₈ alkoxy, C₃₋₈ cycloalkyloxy, C₅₋₈ cycloalkenyloxy, C₂₋₈ alkenyloxy, C₂₋₈ alkynyloxy, C₁₋₈ alkylthio, C₃₋₈ cycloalkylthio, C₅₋₈ cycloalkenylthio, C₂₋₈ alkenylthio, C₂₋₈ alkynylthio, C₁₋₈ haloalkyl, C₁₋₈ haloalkoxy, C₁₋₈ haloalkylthio, C₂₋₈ haloalkenyl, C₂₋₈ haloalkenyloxy, C₂₋₈ haloalkenylthio, C₂₋₈ haloalkynyl, C₂₋₈ haloalkynyloxy, C₂₋₈ haloalkynylthio, phenyl which may be substituted, phenyl C₁₋₄ alkyl which may be substituted, benzylthio which may be substituted, benzyloxy which may bo substituted, phenoxy C₁₋₄ alkyl which may be substituted, phenoxy which may be substituted, phenylthio C₁₋₄ alkyl which may be substituted, phenylthio which may be substituted, benzoyl which may be substituted, benzoyl C₁₋₄ alky which may be substituted, benzoyloxy which may be substituted, benzoyloxy C₁₋₄ alkyl which may be substituted, naphthyl which may be substituted, 5 or 6 membered heterocyclic ring which may be substituted, C₁₋₈ hydroxyalkyl, C₁₋₈ hydroxyhaloalkyl, C₁₋₆ alkoxy C₁₋₄ alkyl, C₁₋₄ haloalkoxy C₁₋₄ alkyl, C₁₋₆ haloalkylthio C₁₋₄ alkyl, C₁₋₁₀ dialkoxy C₁₋₄ alkyl, C₁₋₃ alkylenedioxy C₁₋₄ alkyl, C₁₋₆ alkylthio C₁₋₄ alkyl, C₁₋₁₀ dialkylthio C₁₋₄ alkyl, C₁₋₃ alkylenedithio C₁₋₄ alkyl, C₁₋₆ alkoxycarbonyl, C₁₋₆ haloalkoxycarbonyl, C₁₋₆ alkoxyoxalyl, CHO, CO₂H, C₁₋₆ alkoxycarbonyl C₁₋₄ alkyl, C₁₋₆ haloalkoxycarbonyl C₁₋₄ alkyl, NH₂, C₁₋₆ alkylamino, C₁₋₆ alkylcarbonylamino, C₁₋₆ alkylcarbonylamino C₁₋₄ alkyl, C₁₋₆ haloalkylcarbonylamino, C₁₋₆ haloalkylcarbonylamino C₁₋₄ alkyl, C₁₋₆ alkoxycarbonylamino, C₁₋₆ alkoxycarbonylamino C₁₋₄ alkyl, C₁₋₆ alkylsulfonylamino, C₁₋₆ alkylsulfonylamino C₁₋₄ alky, C₁₋₆ haloalkylsulfonylamino, C₁₋₆ haloalkylsulfonylamino C₁₋₄ alkyl, C₁₋₆ dialkylamino, C₁₋₆ dialkylamino C₁₋₄ alkyl, C₁₋₆ dialkylaminocarbonyl, C₁₋₆ dialkylaminocarbonyl C₁₋₄ alkyl, C₂₋₆ alkyleneimino C₂₋₆ alkyleneimino C₁₋₄ alkyl, C₂₋₆ alkyleneiminocarbonyl, C₂₋₆alkyleneiminocarbonyl C₁₋₄ alkyl, C₁₋₆ alkylcarbonyl, C₁₋₆ alkylcarbonyloxy, C₁₋₆ haloalkylcarbonyl, C₁₋₆ haloalkylcarbonyloxy, C₁₋₆ alkylcarbonyl C₁₋₄ alkyl, C₁₋₆ alkylcabonyloxy C₁₋₄ alkyl, C₁₋₆ haloalkylcarbonyl C₁₋₄ alkyl, C₁₋₆ haloalkylcarbonyloxy C₁₋₄ alkyl, hydroxyimino C₁₋₄ alkyl, C₁₋₆ alkoxyimino C₁₋₄ alkyl, C₁₋₆ alkylcarbonyloxyimino C₁₋₄ alkyl, C₁₋₆ alkylsulfonyloxyimino C₁₋₄ alkyl, C₁₋₆ alkylsulfoxy, C₁₋₆ haloalkylsulfoxy, C₁₋₆ alkylsulfoxy C₁₋₄ alkyl, C₁₋₆ haloalkylsulfoxy C₁₋₄ alkyl, C₁₋₆ alkylsulfonyl, C₁₋₆ haloalkylsulfonyl, C₁₋₆ alkylsulfonyl C₁₋₄ alkyl, C₁₋₆ haloalkylsulfonyl C₁₋₄ alkyl, C₁₋₆ alkylsulfonyloxy, C₁₋₆ haloalkylsulfonyloxy, C₁₋₆ alkylsulfonyloxy C₁₋₄ alkyl, C₁₋₆ haloalkylsulfonyloxy C₁₋₄ alkyl, C₁₋₆ haloalkoxysulfonyl, C₁₋₆ haloalkoxysulfonyl C₁₋₄ alkyl, C₁₋₆ dialkylsulfamoyl, C₁₋₆ dialkylsulfamoyl C₁₋₄ alkyl, C₁₋₆ alkoxysulfonyl, C₁₋₆ alkoxysulfonyl C₁₋₄ alkyl, C₂₋₆ cyanoalkyl, CN, C₁₋₆ thiocarbamoyl, C₁₋₆ nitroalkyl, NO₂ or halogen, or two of R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰ and R¹¹together are C₁₋₃ alkylenedioxy which may be substituted, or C₃₋₆ alkylene, which comprises reactins a compound of the Cormula (2) A-H  (2) wherein A has the same meaning as defined above, with a compound of the formula (3)

wherein R¹, R² and Y have the same meanings as defined above, and X is a halogen; reacting a compound of the formula (4)

wherein B and Y have the sane meanings as defined above, with a compound of the formula (5) R¹R²NSO₂X  (5) wherein R¹ and R² have the same meanings as defined above and X is halogen; or a compound of the formula (6)

wherein R¹, R², A and Y have the same meanings as defined above, with an oxidizing agent, wherein the phrase “which may be substituted” means that optional inclusion of one or more substituents selected from the group consisting of halogen, C₁₋₈ alkyl, C₁₋₈ haloalkyl, C₁₋₈ alkoxy, C₁₋₈ haloalkoxy, C₁₋₈ alkylthio, C₁₋₈ haloalkylthio, C₁₋₆ alkylsulfoxy, C₁₋₆ alkylsulfonyl, CN, NO₂ and C₁₋₆ alkylcarbonyl, the number of the substituents is 1 to 5, and the substituents may be identical or different). 